Dane Cook, 50, is engaged to his girlfriend of 5 years, 23-year-old Kelsi Taylor

In 2018, we learned that Dane Cook – who was then 45 years old – was dating a 19-year-old, Kelsi Taylor. That year, he kept on talking about their relationship and how much he loved his teenage girlfriend and how they’d actually known each other for a while because she came to one of his “game nights” when she was likely just 16 years old. That’s why Dane kept emphasizing that they were “friends first,” because he groomed a 16-year-old for a few years before they officially began dating on her 18th birthday. Back when Kelsi was 20 years old, Dane claimed he already thought of her as his wife, even though he’s famously marriage-phobic. Which brings me to this: 50-year-old Dane Cook proposed to Kelsi, who is now 23 years old. She said yes.

Dane Cook is newly engaged! The Good Luck Chuck actor/comedian proposed to his singer/fitness instructor girlfriend Kelsi Taylor after five years of dating, PEOPLE can exclusively reveal. Cook popped the question to Taylor on Wednesday, July 13.

“I was so ready to ask her. I was completely zen about it,” Cook, 50, tells PEOPLE in this week’s issue. “The evening of the proposal was incredibly beautiful, the weather was perfect, sunset was spectacular, and I was just quite simply very happy…. I was asking my best friend, the woman who I’ve shared some of the greatest times of my life with, to marry me so we can start the next chapter our of lives together. I was also thinking of how absolutely stunning she looked.”

Meanwhile, Taylor, 23, says she couldn’t believe it was happening: “The second he began to reach for his back pocket, my stomach flipped. I couldn’t have asked for the moment to have been more perfect. All that was going through my brain was, ‘Wait, is this actually happening right now? Is he proposing?’ I was also just really focused on what he was saying to me because I was trying desperately to etch the words into my brain,” she continues. “They were so beautiful, I really wanted to soak it in.”

Cook says it was the “best feeling ever,” and, afterward, “We sat together on the deck, shared laughs, held hands and watched that giant moon sparkle across the ocean.”

Cook says he’d been planning the proposal for months and decided to do it on a trip to York Beach, Maine, which holds a “special place in our hearts.”

“When we started dating, we went there on our first trip together so to return five years later was meaningful to us,” he says. “It’s a place I spent much time in growing up so I have such fond memories there. After my mother passed away, she asked me and my siblings to release her at her favorite spot, the breathtaking location, at the tip of Cape Neddick Point, Nubble Lighthouse, where our vacation cottage is located. It felt like the right place.”

Adds Taylor, “The fact that he had been planning this for months, designed the ring and coordinated everything so seamlessly without me knowing was just blowing my mind. It was such a pinch-me moment. I hugged my mom and couldn’t wait to FaceTime the rest of my family and share the news. My family loves him so much so they were beyond excited for us.”

[From People]

“When we started dating, we went there on our first trip together so to return five years later was meaningful to us.” He took her to Maine when she was 17 or 18 years old, I guess. I think that violates some interstate human trafficking laws. Anyway yes, this is a “longtime romance.” They’ve been together for five years. Officially, they began dating the second she turned 18. I mean… it sounds like she has a job and a life away from him a little bit, which is good. But lord, this is a mess. I feel sorry for her.

Photos courtesy of Kelsi’s IG and Dane’s IG.

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124 Responses to “Dane Cook, 50, is engaged to his girlfriend of 5 years, 23-year-old Kelsi Taylor”

  1. Celeste says:

    I would be devastated if I were her parent.

    • dina says:

      honestly tho

    • Laughysaphy says:

      Apparently they met when her dad brought her to Dane’s game night. Ugh.

      • Mary Tosti says:

        That’s disgusting.

      • Emily says:

        It’s somehow worse that Dane is her dad’s friend. I can’t imagine at 17 having any interest in an OLD MAN who hangs out with my DAD.

        It feels like old times when parents paid someone to marry their daughter. “Here, take my daughter to cover my poker losses.”

        I feel SO bad for her. She’s been groomed. She’ll be caring for an old man when she’s in her 40s, her youth wasted.

    • Lolo86lf says:

      We don’t know how her parents feel about her daughter marrying a men so much older but just hear me out: He is worth $35 million dollars according to Google and her parents may be pleased that she is going to be financially secured. Just saying.

      • Lou says:

        Dude, this isn’t 1950. She’s taking formative time away from developing her own identity, and it seems like skipping college, to be with this creep. It’s a completely short term mindset to think the financial security she’ll gain is worth the loss she’ll experience from being groomed like this.

      • Miranda says:

        They might approve because he offers “financial security”? They’re supposed to be her parents, not her pimps.

      • Tiffany:) says:

        But no doubt HE has great lawyers that can draft a prenup. Just because he’s rich doesn’t mean she’s going to get much if they breakup.

        He’s dominated the time in her life where she should be meeting different kinds of people and having a variety of experiences. I’m really sad for her. At the same time, I probably would have been blown away by the love bombing and luxury at that age, too.

      • MoonTheLoon says:

        @Tiffany- Even if he doesn’t, all he has to do is establish residency in whichever states divorce laws are more advantageous, 6 months previous to filing. Rich guy like him can easily manage that. Especially if she’s in love and he convinces her. Pre-nup, of course, is more advantageous still and he’ll likely do that to save hassle.

      • Tiffany:) says:

        True, Moon. Also, the vast majority of his money was made before the marriage, so she’d have no stake in that. Marrying him would not produce the payoff some might assume.

    • Both Sides Now says:

      @ Celeste, that was my first thought too! And she was happy about this? You have got to be kidding me…..

      As for his role in Good Luck Chuck, he’s going to need all of the luck in the world for this marriage to work out.

      She’s a fool too.

    • DouchesOfCambridge says:

      Seriously she’s 23 and they’ve been out together 5 years? This makes me sad for her and I feel like he’s such a predator… If i’d be her parents i’d be freaking out but after hearing about their engagement, i’d be so so so sad.

    • Andrew's_Nemesis says:

      I mean, ew. Ew ew ew ew ew ew EW. Just totally revolting and tragic.

  2. dina says:

    He grosses me out so much, yuck. This poor girl.

    • StellainNH says:

      He’s been with her for five years and she’s only 23 years old?? What a dirty old man, grooming a child.

      • MeganC says:

        He isn’t a dirty old man, he is a pedophile.

      • JesMa says:

        Eh, technically an ephebophile which is an attraction to adolescents usually 15-19. The most distressing part is that I think more than half of men fall into this category. The popularity of teen or barely legal porn is disconcerting. So many times in popular culture there is a fixation of when famous girls turn 18. It is gross.

      • Tan says:

        @JesMa – pls no technicalities- I’ve heard the term Ephebophile and Hebephile used multiple times as excuses for adults who basically take advantage of minors and excusing the behavior since the child wasn’t under 5 years old

      • JesMa says:

        I’m not defending him, but is a difference between being sexually attracted to a 4 year old child versus a 17 year old child. Both are still wrong, but a pedophile is not interested in children that have gone through puberty. Also while gross, most states allow adults to have sex with adolescents from 16-19. I actually think most men feel comfortable stating their attraction to teenagers. It always turns my stomach and I always call it out. Dane Cook for sure took advantage of this poor girl.

  3. Laughysaphy says:

    Disgustinnnggggg! “People are like, ‘You’re robbing the cradle,’ and I’m like, ‘She hasn’t been in the cradle for nine years,’” he said to sparse laughter during a 2019 appearance on Jimmy Kimmel Live!”

  4. Aurora says:

    I wonder if they plan to have kids. People are critical of women who have babies at “advanced” ages but no one bats an eye at middle age men becoming dads.

    • Lolo86lf says:

      If they want kids they better hurry up because men in their fifties are less likely to produce viable sperm.

  5. Talita says:

    I’m 37 and I can’t picture myself marrying a 50 year old.

    • Lolo86lf says:

      But what if you fall in love with him though.

      • North of Boston says:

        But what if you have “a mature soul” or “old eyes”? /s

        I am eye rolling him (again) so hard, and David Duchovny and the lot of them. I just figure they are too weak and insecure to deal with having a peer for a partner or lover. Big dopey man babies.

      • North of Boston says:

        But what if you have “a mature soul” or “old eyes”? /s

        I am eye rolling him (again) so hard, and David Duchovny and the lot of them. I just figure they are too weak and insecure to deal with having a peer for a partner or lover. Big dopey man babies.

      • H says:

        I’ve been a fan of Duchovny’s forever and also find it revolting he’s dating a woman half his age (like a little bit older than his kids). I don’t get it with these guys. How can you have anything in common with someone who doesn’t have the same life experiences you do?

      • eliza says:

        Liev Schreiber +1

    • Andrea says:

      I am 41 and could see myself with a 57 year old, but that’s the difference, we both are grown adults who have had many lived experiences. Her only experiences may have been with this creep.

      • Deering24 says:

        H, none of this is about these guys forming truly healthy relationships. It’s all about proving their dominance and studliness. They love their egos, not these women. And Duchovny has been problematic for a while–Californication alone seemed like a real expression of his mindset.

  6. Lolo86lf says:

    Wow, 27 years difference is a huge gap. I don’t know what to say. She is 23 years old now but we know that women’s minds are always more mature than a male counterpart of the same age so she knows what she is doing. Also her family surely explained to her the pros and cons of marrying someone old enough to be her father. Isn’t he embarrassed to be with a woman so much younger? Anyway I wish them well.

    • C says:

      No, I don’t think that at 23 she knows what she’s doing in the sense of knowing what’s really going on or what it’s going to look like 20 years down the road. And you’d be surprised at how many families don’t bother to explain that kind of thing, and I doubt hers did since he groomed her and apparently nobody bothered to do anything about it.

      • Lolo86lf says:

        In 20 years Cook is going to look like a prune and she will still be young lol. I refuse to believe that in five years of courtship neither family nor friends pointed out to her the drawbacks of dating/marrying a man 27 years older. Grooming means brainwashing in this case and boy did he groom the hell out of her.

    • Zapp Brannigan says:

      “we know that women’s minds are always more mature than a male counterpart of the same age”

      This is a centuries old excuse that explains away why young girls, then women are expected to be the one that carries the domestic load, give up their youth to having children by older men, then spend their mid life caring for men older than their own fathers, then finally they have the sweet release of death to look forward to after a life of drudgery caring for, cleaning for and picking up after everyone else.

      If this young woman was my daughter I would be dragging her out of their by her ponytail, handing her a plane ticket and some cash and telling her to go and live her life, not be an ornament for some mid life crisis in chinos.

      • Lolo86lf says:

        I agree with you generally speaking but in this particular case she is not a young girl, she is 23 years old in the 21st century. I understand they started dating when she was 18 years old but 5 years passed and she had plenty of times to think about her relationship with Cook. She is too young for him but he must have showered her with flowers and chocolates and diamonds and romantic dinners and romantic get aways these past 5 years until she fell in love with him.

      • Amanda says:

        “… not be an ornament for some mid life crisis in chinos” …is such a great line!!

      • Jc says:

        I have to disagree that Cook will look wrinkled and prune! He is seriously tweaking his face and he will have a tight botoxed and lifted face. His face just looks off.

      • Chaine says:

        Jc you are so right, the amount of cosmetic work he has had done actually makes him look older than fifty though. She is still going to look like she is with an older guy, just a weirdly insecure puffy one rather than a wrinkly one.

      • Turtledove says:

        “I would be dragging her out of their by her ponytail, handing her a plane ticket and some cash and telling her to go and live her life, not be an ornament for some mid life crisis in chinos.”

        Preach it from the rooftops! YES! She has been with him since she was 18. And is now going to marry him. She is missing out on experiencing being a young adult on her own. She will NEVER get that back. He is a complete creep. The fact that she was underage when they met and started dating the second she turned 18 is HIGHLY sus.

      • Nic919 says:

        If she met him at 23 that’s one thing but she met him at15 and he’s been grooming her since then.

        Her parents sold her out.

    • LilacMaven says:

      She may be 23 now, but they first met when she was 15 years old.

      They started dating on virtually the same day she turned 18. I doubt that’s a coincidence.

      Yeah, I think grooming was definitely involved between the ages of 15 and 18.

  7. Ariel says:

    Yuck

  8. Plums says:

    literally said “ugh” out loud when I saw the headline and picture. But then reading to find out it’s even worse and that he groomed her from a teenager. he’s so gross.

  9. greenmonster says:

    Dear Kelsi, aim higher! Just because Leonardo is in a relationship doesn’t mean you have to settle for THIS.

  10. libellule says:

    I was feeling gross when a 23 year old was trying to date me (I’m 32) and I told him the age difference was too much for me now.

    The guy is a creep

    • L84Tea says:

      When I was 23 I dated a guy 11 years older than me. Yeah, the gap was just too big for me. I didn’t think it would be that big a of a deal, but it was.

      • Andrea says:

        When I was 25, I dated a 36 year old divorcee. He thought I was too immature, he was too controlling. Didn’t want me wearing makeup or nail polish because it could lure in men. He disapproved of me having guy friends. His wife cheated on him with his brother (this sounds like a country song) and despite therapy and it being 6 years, had deep seeded issues from it. I ultimately broke up with him after 4 months. My friends didn’t like how he treated me. He ended up marrying a tomboy woman, which I believe made him feel secure since she never wore makeup or nail polish lol.

  11. Mothra says:

    Love is so beautiful.

  12. Jessica says:

    So much grossness on so many levels. He is so gross and creepy and yes, they were definitely dating before she was “legal”. Ick. Didn’t he also date Jessica Simpson when she was pretty young? Not THAT young but I remember thinking it was weird and creepy and this is a whole other level.

    • Laura says:

      Yeah this whole Leo/Dane excuses of “didn’t start dating til she was 18” is horse shit. They’re obviously active in their lives and making their moves earlier than that, aka grooming.
      The fact that her Dad allowed this to happen is gonna hit hard when she’s older and has popped out several of his kids, and he’s cheating on her with another 18 year old. This is fucking foul.

  13. girl_ninja says:

    He no only looks old enough to be her father he IS old enough to be her father. Knowing they went on this sojourn to Maine all those years ago suggests that he groomed her. Disgusting and sad.

  14. Rakely says:

    This makes me feel sick to my stomach. I feel so sorry for this young woman. Someday it will dawn on her how gross this is. Look how things turned out for Courtney Stodden.

    • AmyB says:

      @Rakely Perfectly said!! Courtney finally realized she was groomed and preyed upon! And I am certain this young woman will too!! This creeps me out on so many levels! Especially knowing he knew her so young, before they even got involved – UGH!!!

    • Lucy says:

      Came here to say this. Someday she will realize what was taken from her and how she was failed. I hope he still has $$$ she can take with her when that happens

  15. HandforthParish says:

    The fact that they say they were ‘friends’ for a long time before dating makes it even more seedy.
    What 40-odd year old man is friends with a teenager? You’d be friends with her dad, not her.

    • Formal Gumby says:

      @Handforthparish you are so right. A 40 year old, friends with a teenager. For some reason, you saying that made it really click for me. This is utter madness. Idk what I’d even say to a teenager, never mind having a dating or wooing-worthy conversation. This is madness.

      Not a half hour ago, I saw a video with Dane on a podcast talking about his his brother stole millions of dollars from him. The brother was acting as his business manager, and was literally creating fake statements in Microsoft word to give to Dane. Among other things, Dane said he never checked his accounts and didn’t know it was happening. I could see him having a teenage mentality; like, his focus and development as a person hovers in an arrested development kind of area. So an insanely younger woman could actually fit. I’m not saying this is right. But to any questions of what do they talk about, an older woman may have a variety of interests and experiences, and he might be mono-lane.

  16. K says:

    I truly feel that a large chunk of themalepopulation (in general but also esp in the case of Dane) is revolting. It is always interesting how so many try to hide it..but they just don’t want to change. They have no shame.

  17. K says:

    I truly feel that a large chunk of themalepopulation (in general but also esp in the case of Dane) is revolting. It is always interesting how so many try to hide it..but they just don’t want to change. They have no shame.

  18. Mooney says:

    I’m 23 myself and I can’t imagine marrying someone twice my age. Ugh 🤢

    • Another Anna says:

      I’m 33 and the idea of marrying a 50 year old is a hard pass.

      Men like this are so pathetic. They don’t have the substance to date fully-grown women and so they go after girls who can’t spot them for what they are. Men 50+ go get some therapy 2022 challenge.

  19. Valar Dohaeris says:

    I recently found out that a 37 year old friend of mine was secretly seeing a 22 year old girl, and I was grossed out. This? There are no words.

  20. Jessamine says:

    “Started dating when she was 18” just reminds me of that Chris Rock bit about when a job pays minimum wage it means they’d pay you less if they could 🤢

  21. Miranda says:

    With age differences like this, I always wonder, “what do they even TALK about? What could she possibly see in someone his age?” And I think we’ve all seen his stand-up, so we know damn well she can’t use the old “he makes me laugh” line.

    • Wendy says:

      A couple of years ago I was very briefly dating a guy in his mid 30’s who dumped me for a 21 year old he found on Tinder — he openly acknowledged to me that most of the time he had no idea what she was talking about and vice versa, that he did a lot of nodding and smiling and waiting for her to be quiet, and that being with her meant enduring things like wild emotional meltdowns and being forced to watch hour-long YouTube compilations of old Vine clips so that he’d understand her references… but that he’d been such a huge loser in high school and deep down inside he still felt like a loser, and being with her was like a wish fulfillment thing for that part of him.

      Anyway, last I heard, they’re still together and spending their weekends playing drinking games while they watch her favorite cartoons from her childhood.

      TL;DR — lots of weak, damaged men out there trying to heal themselves with barely legal women’s bodies.

  22. @poppedbubble says:

    Yuck. Then ewww. Then yuck some more and another ewww!

  23. Lady Luna says:

    That top picture looks awful. He’s so gross.

  24. B says:

    Can you imagine how visits to derm/plastics go?

  25. AnneL says:

    Ugh. It would be bad enough if they MET when she was 23 and he 50, but at least then she would have been an adult, sort-of/technically, when he set eyes on her. But she was an underaged teen! Blech.

    Well, I hope she gets what she wants out of it. If in ten years she wants to nope out of being married to a 60+ man who set his sights on her when she was too young to know who she really was, I hope she does so with some $$$ and a clear sense of self.

  26. Davi says:

    How is it “interstate human trafficking” when they were in a consensual relationship and she was 18? LOL

    I once went with an older friend (the older brother of an ex), when I was about the same age on a trip across state lines for him to pick up his new pet. Does that also mean that I was being “trafficked”? Good grief.

    • poppedbubble says:

      Keep on believing that he waited until she was 18 before they started having sex. And yes, you would haven trafficked if you were the same age as her when they met and this friend took you across state lines and had sex with you.

  27. MY3CENTS says:

    How many times has she been mistakenly called his daughter?
    Not enough.

  28. marietta2381 says:

    Other than the fact this man is disgusting and Kelsi should run the hell away from him, I’ve always found him to be creepy… But Man he has NOT aged well at all. I can’t believe anyone hasn’t told this woman what she’s up for if she marries him…

  29. SIde Eye says:

    This frigging grossness before I even had my coffee and the mental gymnastics people are doing to justify this douchebaggery is astounding. This is all kinds of what the f***ckery. I don’t even have enough side eyes for her parents.

    They met when HER FATHER brought her to his game night as a teenager. He then felt as a douche canoe in his FORTIES he should befriend a teenager. Because what 40 something doesn’t have teenage friends? I mean, there’s so much to talk and text about! Especially cause she’s “so mature” an “old soul” (massive eye roll).

    He started dating her when she was 18 – or maybe before. He groomed a teenager in his mid forties. The f*** nerve of him to act this is something we should celebrate.

    She is going to be changing his diapers when she is just in her 50s. She is going to play nursemaid to this assclown only to have no one reciprocate when it’s her turn. When she looks back on this at 50, she will understand how creepy this is. This is next level creepy.

    I have a teenager. If a 40 something started texting them and befriending them I would take these earrings off and throw down. You think Cate Blanchett got her ass kicked by that Irish mom in that movie with Judie Dench – nah that pedo may not make it out of that confrontation alive.

    I can’t today. Wtf? Times a thousand.

    • Eurydice says:

      I think he likes old souls as long as they’re in young bodies. Either he dumps her when she starts losing her freshness, or she dumps him when he evolves from father figure to grandfather figure. Either way, she won’t be changing his diapers when she’s 50.

      • SIde Eye says:

        @Eurydice I really hope you are right! I hope for her sake it ends before there are children involved – he would not even be around to see his kids graduate from hs or college. When are these 20 somethings going to learn that these 40-70 year old men are Creepy McCreepertons that the 40 year olds don’t want because we are on to them. They HAVE to date this young. They also want women this young because of the control. This is especially true for the rich ones – they want a young person to control who will not be on to them. When I was 20 something the 50 year old men that approached got laughed at – I don’t care how rich you are -you are old enough to be my fahter/grandfather – this is next level gross – take your Benz, your apple martini, and dry crusty balls and get the hell out of my face. I’m astounded these old dudes and their assclownery is getting any play from young women and good looking young women at that. Up next Carrot Top marries a 19 year old supermodel…I really can’t today.

    • Lolo86lf says:

      I am not sure how you expect her parents and friends to act and or do at this point. It’s too late. She has decided to marry him and people in her life don’t want to ruin her happiness. Perhaps they all tried to dissuade her from dating him to no avail. He won her over and only the future will tell what’ll happen. Look at Aaron Taylor Johnson married to a much older woman for ten years.

      • SIde Eye says:

        @Lolo86if You’re correct that it’s too late now. The time to act was when their teenager was being befriended by a 45 year old douchey Botoxed creeper. But her dad was hanging out at Dane Cook’s game night and thought it would be a good idea to bring his teen daughter. So that pretty much says everything I need to know about her dad right there.

      • TEALIEF says:

        Given the adults around her failed in their duty of care, and their duty to care, my thoughts went to her friends. Where were her friends, and the people in her peer group? Given the experiential and economic imbalances, she’s going to need a few solid friends to run some welfare checks, and to fall back on. This relationship started improperly, and seriously sideswiped actual legal guard rails. This man is as corrupting as he is loathsome.

      • SIde Eye says:

        And this was my thought as well @Tealief where are her friends? This entire story is infuriating. You’re right that he is loathsome.

    • JustBe says:

      Thank you so much for this comment!!
      I cringed at every aspect of this story.
      Her father took his cute, petite teenage daughter into the den of a known creep and is likely celebrating at winning the lottery with the infusion of payoff money currently being lavished on the family.
      Cook has been grooming this young woman for all of these years. He is training her to be exactly who he wants her to be: incurious, nonjudgemental, with her world revolving solely around him. This isn’t a life so much as an existence from a gilded cage. She won’t know who she is outside of her relationship with him, drastically reducing the chances that she’ll ever leave or risk disappointing him.
      It also saddens me that so many dismiss the yuck factor because of his money, like this woman will ever have any real access to that money to do as she wishes without his explicit approval.
      We often view these relationships as being an issue because the man doesn’t want to grow old, but this is about a man not wanting accountability or any expectations of maturity.

  30. TheOriginalMia says:

    Gross. She’ll regret this when she gets older.

  31. Sean says:

    I’m still 10+ years away from 50 and I can’t even imagine dating a 23 year old. Given that it’s Dane Cook, I’m sure they’re close in age emotionally speaking but just no…on so many levels.

    I hope she or someone close to her wakes her up to the realities before she’s wasted too much of her life on him.

    This may just be me but the older I get, one of the things I want most is a partner who’ll enjoy and understand the same cultural references I do. How does being with a 23 year old when you’re 50 NOT remind you that you’re well, significantly older?

    I know these men do it because they’re desperate to hang on to their fleeting sense of youth but at some point I’d think it’d just be a reminder that you’re not young anymore.

    • Honey says:

      You know . . . when I was a teenager coming into my twenties, my great-grandmother once told me “it’s better to be an old man’s darling than a young man’s fool.” That stayed with me all of my life. However, I’ve never practiced it. Me then at her age versus me now nearing his age is still like “🤢 his old a$$ is 50!” The age dynamic is personally too much for me.

  32. MaryContrary says:

    As the mother of young adults in this age group: vomit.

  33. AppleCart says:

    Seeing his brother stole millions from him and went to prison for it. I assume there will be an iron clad pre-nup. But it also seems like he does not have much family. And may cling to her for the family dynamic. I’m 51 and realizing life does not go on forever… He will need someone to help him leave this mortal coil. I know plenty of men who have gotten married to not die alone.

    But basically he grew a wife like a Chia Pet.

  34. LIONE says:

    So basically he’s as emotionally mature as a 18 year old. Great!

  35. Chaine says:

    I had a friend for a while who had a marriage with this age disparity. It was great when she was young and had a suave older husband who was already financially stable, socially elite for their town, and his connections helped her career. But by the time she reached her early forties, hubs was in his seventies and decrepit, colon cancer, a heart attack. She was feeling like she was in the prime of life, wanted to travel (they never had kids) and socialize, but instead she was spending a lot of time in doctor offices and hospitals and helping her hubs transfer from bed to potty chair. We would go out somewhere for drinks at happy hour and he would be calling her all querulous voiced because he couldn’t remember when to take his meds, or wanted to know when she would be back because he was tired and needed her to help him upstairs. It was miserable for her and she ultimately had several affairs and then divorced him when he was 77 and she was 50 to marry someone else, which struck me as totally cold hearted, but I guess that she hadn’t considered going in to it that she would one day be babysitting a granddad.

    • SIde Eye says:

      @Chaine – thank you for sharing this. This is an account every young woman should read. I know someone in a similar situation – only she didn’t divorce. He is in his 90s now and she at 64 is still taking care of him. Instead of traveling in her best years when she was in her 40s, 50s, and now in her 60s – she was in hospitals, at chemo, at various doctors offices. Her few nights out sound exactly like your friend – constant interruptions about something he forgot and why are you out when you should be taking care of me. He broke his hip for the second time last year and she can barely lift him from bed to potty. Her parents aged at the same time as her husband, and she takes care of all three of them. Once I saw her and asked how she was doing and she just burst out crying at the grocery store – the toll of everything catching up to her at once. I suggested she hire some help (she can afford it) but her hubby keeps firing everyone she hires and asking for his wife. I bet if she could go back she would go back to that moment when she was 25 and her husband approached her to introduce himself and run away.

    • AmyB says:

      @Chaine @SIde Eye

      These stories are truly the reality these very young women face by marrying men several decades older than they are. Yes, it fine in the beginning, but when they get to their prime – and it really is the case that we women get to our prime in our 40s!! – these men will be in their 70s or older. Facing health issues and no longer the suave, charismatic men they married that can keep up with them. And perhaps before that, these young women may realize how they were truly robbed of their youth (like a Courtney Stodden, Megan Fox) and have serious resentments).

      I personally could never date or be in a serious relationship with someone much younger/OR much older. 10 years would be the max for me, either way. I am divorced, 53 now with a 21-year-old daughter. I am in a very fulfilling relationship now for the last three years with a man who is 60. When I was in my early 40s, I briefly dated a guy who was 29 lol. The sex was great, but other than that, NOTHING in common so I cut that short. And that was only about a 12-year difference. These vast age difference have such a power dynamic imbalance; it is just unhealthy in my eyes. End of story.

  36. Emily says:

    I feel bad for her. She doesn’t realize what she’s missed out on. In ten years, she’ll be pulling a Megan Fox, trying to have the youth she didn’t because she was groomed by an old man.

  37. Jessica says:

    I forgot to mention in my earlier post, I went to high school with a girl that had a relationship with and ended up marrying the Math teacher. She waited until she was 18 (no she didn’t) and he was 47. He and his wife were friends
    with her parents as well as him being her teacher and soccer coach. The wife obviously divorced him when the initial affair came out. They got married and had kids. I believe they are still together. It wasn’t very scandalous at the time..but it should have been.

    • Emily says:

      That man hopefully doesn’t have a teaching career anymore. He cannot be trusted to be around children without abusing his position.

  38. Ann says:

    Even reddit thinks DC is gross. That’s something. I admit I did find him funny during his prime. I was in college and everyone loved him. It’s not like some tragic fall from grace but I still didn’t expect him to go the bad face-lift groomer route. Ick ick ick.

  39. NotSoSocialB says:

    Everything about this is so OTT gross.

  40. Lizzie Bathory says:

    My sister & 2 of my female cousins have 15-25 year age differences in their marriages, which is a bit unusual but they’re all very happy. But in each situation, the women were well into their thirties & had been previously married, so they knew what they wanted in a relationship. This seems like…not that.

    I wouldn’t be surprised if Dane Cook is feeling his age or if he proposed because she’s at the age where she wants to have fun & discover herself as a young adult. Either way, I don’t see this being a happy union.

    • Turtledove says:

      “But in each situation, the women were well into their thirties & had been previously married, so they knew what they wanted in a relationship. This seems like…not that.”

      Yes, I think that makes a huge difference. An age gap in and of itself is not always an issue. But in this case, she was so young when they started, possibly even underage, and that is really where it gets icky. I just feel like she was hitched to this much older man the second she became a legal adult. No time to just be a young woman and do her own thing.

  41. Bobbie says:

    Middle-aged men wouldn’t be able to get away with this ridiculousness if there weren’t women out there who went along with it.

  42. Ramona says:

    Many of these men celebrities are dating much younger: Duchovny(61) and his 29 girlfriend,Jake Gyllenhaal(41) and 26 year old girlfriend,John Hamm(51) and his 34 year old girlfriend,Casey Affleck(46) with his 24 year old girlfriend,Zach Braff(47) with Florence Pugh(26)…
    Naomi Watts and Liev Schreiber are separated :Naomi is with Billy Crudup(both 53) and Liev(54) dating a 29 year old.Do these men lack emotional maturity to deal women their age? Or do they want to feel younger? Or is it a control thing ?🤷‍♀️ I don’t know but I find it super creepy.

    • Gah says:

      Can only speak to the liev situation.

      His girlfriend is a total hoot and financially independent. She tends to hang w an older crowd of awesome women and is a huge part of his kids’ lives. I too side eyed the new model bc she’s a foot taller and 20 years younger version of Naomi Watts and assumed he was ahem taking care of her. Not the case.

      And let’s just say he’s age agnostic but pretty into blondes when he’s single…

      As for the other dudes…mostly seem creepy.

      There are 18 years between me and my hubs but he looks really young which is super annoying as I get older. He’s technically a boomer and I’m a very old millennial but we got together when I was 30 and had lived a LIFE. I had no intention of marrying ever haha

  43. K8erade says:

    In response to @ramona but just my overall experience with these kinds of relationships. In my experience, it’s both emotional maturity and control.

    I dated someone like this in the industry when I was 20 and he was 33. He was incredibly controlling and the relationship descended into emotional and verbal abuse and was becoming physical (I won’t lie, I became reactively abusive myself) and I broke it off 4 years later and moved on with someone else. These men want a woman who is willing to constantly stoke their ego and will tend to their needs 24/7. The younger and more innocent a woman is the more willing she is to be “trained” to do so.

    Dane Cook has been notorious for creepily chasing after young women but in this day and age he knows he’d get called out. We’ve all known he’s a creep since 2011. See how their relationship began at the beginning of #MeToo? He’d rather pay for her to get plastic surgery to look forever young than get called out for being a creep at this point. It’s all about optics for him. I doubt he truly cares about her in any kind of meaningful depth. He’s just that kind of guy.

  44. HeyKay says:

    The best advice I ever got from an older and beloved family member was “Be very careful who you marry. Enjoy a long engagement, spend that time truly getting to know each other. Do not plan a wedding, plan a marriage.”

    Dane Cook = Creep!
    Kelsi = Too young and inexperienced to fully understand what kind of BS is being shoveled at her.
    Dad of Kelsi = PMK in training. Basically Dad brought her to a pedo/groomer, made her available and encouraged this.

    The statement “my family loves him” in this situation, makes me sick.
    No, they are infatuated with his money, and the lifestyle his money can bring to you and by extension, them. Sickening. It’s like the old fashioned idea of you marry the daughter off to a rich man and that raises the entire social cache of her family.

    Maybe she’ll get lucky and Dane Cook will die shortly after the marriage.
    More likely? Dane Cook will divorce her within a few years, making certain to lockdown all his money first. Then wash, rinse, repeat.
    And for her? Not even 30 and divorced and wait until she hits 35-40 and realizes exactly what happened to her.
    Only young once, do not waste it.

  45. jferber says:

    HeyKay, Agree. He will definitely lock down his money. And this bothers me on her behalf. She’s wasting her youth on him and that bitch doesn’t want to give her money? I hope she has a very smart, calculating mother (lol, double-edged sword) to see to it that girl nails down the money angle in the pre-nup. Notice that his arms are twice the size of hers? A lot of steroids. Wonder if he gets ‘roid rage? I hope it’s worth it to you, girl. And good luck.

  46. SIde Eye says:

    Also these pics of them together are beyond creepy! Even those eyebrows are running for the hills towards that receding hairline. She should follow the brows and RUN. @HeyKay your post is spot on.

  47. Rnot says:

    I struggle to keep a conversation going with my 19 year old relatives. The world is so different for them that they might as well be from another planet. I love them to pieces but I cannot imagine trying to start or maintain a romantic relationship with someone so much younger. If you had body hair before they were born then they’re too young for you.

    It is a little jarring to see the strong revulsion for this situation on the very same day that so many commenters here were adamantly insisting that Monica Lewinsky “knew what she was doing” and therefore deserves no respect or sympathy. She was 21 and he was 49. Monica was the wronged party. Kelsi Taylor is the wronged party. Princess Diana was the wronged party. Don’t excuse it.

  48. Andrea says:

    I have heard this exact saying too regarding being someone’s darling and I have a 76 year old friend (I am 41) who dated a man 30 years older than her when she was in her early 30s. His children disapproved and he ultimately died, but he was the love of her life. However, she had some major hangups regarding sex and thus wanted an older man who wasn’t that interested in it and where they had common interests etc. Basically, she wanted a companion who gave her compliments, gifts, and had thijgs in common with her. She never married and has been single 30 years and bitterly so regarding it. She always defends age gap relationships vehemently. She doesn’t seem to understand grooming etc. Because she only sees it from her narrow point of view. To her, young men only want sex and don’t treat a woman like a princess.

  49. LIONE says:

    My clairvoyant grandmother, who does not know this man at all, had one look at their picture together and said: He’s cheating on her.

    I would not be surprised!

  50. jferber says:

    Lione, I love your grandmother. And I bet she’s right.

  51. Luna17 says:

    Definitely a yuck factor. Honestly though, most 23 year olds have no money, zero ability to buy a decent house or maybe even a decent car, student loans, no way to afford decent medical care in many cases. Can you blame a young woman for choosing a rich older dude and a luxury life over working an entry level job 50 Plus hours a week and maybe making $35,000 or $40,000 a year and maybe two weeks vacation? There’s a reason women are having Nick Cannon’s kids and marrying rich older dudes instead of living in poverty while working full time while the rich get richer and the rest of us try to figure out how to afford rent, gas and food. I think this late stage capitalism hellscape we are leaving for younger generations has something to do with this, not just bad parenting or grooming.

  52. Thinking says:

    If he were handsome I might understand this.

    Since I don’t think he is (my opinion) I don’t get this at all.

    He’s only 3 years older than Leo DiCaprio, but for some reason I don’t have as perplexed reaction to Leo and whoever his latest model is. Not saying Leo is handsome like Robert Redford, but his couplings are less baffling to me than this one. I wonder how much the guy’s looks play a part in my reaction to these kinds of couplings. Shallow, I know, but I know I’m
    not having a consistent reaction.

  53. Silent Star says:

    This is giving me Doug Hutchison and Courtney Stodden vibes. 😳

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