Jamie Lynn Spears, 21, is engaged again, this time to Jamie Watson, 30

I had kind of forgotten about Britney Spears’ little sister Jamie Lynn Spears. Did you know that Jamie is only 21 years old? Crazy, right? It feels like she was a teenage mother a decade ago, but Jamie’s daughter Maddie is only 4 years old right now (I think Maddie turns 5 in a few weeks though). When Jamie got pregnant in 2007, she was the star of a Nickelodeon show and best known for being Brit-Brit’s little sister. The Spears family quickly moved Jamie back to Louisiana to have the baby, and from what little I know about her, I think Jamie has been living quietly in Louisiana all this time. She was with Maddie’s father, Casey Aldridge, until 2010. Since then she’s been with Jamie Watson, who is currently 30 years old. Jamie Lynn just announced her second engagement!

Here comes the bride! It looks like there’s going to be a wedding in the Spears family after all — Britney’s little sister, Jamie Lynn, is engaged to her boyfriend of three years, Jamie Watson.

Spears, 21, announced the happy news on Twitter, with an Instagram picture of herself flashing the ring and hugging her fiance, 30. “Guesssss what??????” she captioned the sweet shot.

Minutes later, she posted another photo: a close-up of the huge, round-cut diamond. “He did good,” she wrote, with a smiley-faced emoticon.

This will be the first marriage for the former Nickelodeon star. She was previously engaged to Casey Aldridge, the father of her 4-year-old daughter, Maddie. They split for good in 2010.

Spears’ engagement comes just two months after news of her older sister’s broken engagement. Britney, 31 — married twice before, to pal Jason Alexander and ex Kevin Federline, with whom she has two kids — was set to wed boyfriend Jason Trawick until the couple’s January 2013 split.

[From Us Weekly]

My mind is particularly warped right now because I spent the weekend curled up with The Purity Myth by Jessica Valenti – it’s a book about how damaging and counter-productive all of the “no sex education” programs are and how fetishizing teenage girls’ virginity is simply wrong, and all I can think about now is how different Jamie Lynn’s life could have been. Still, I’m sure she adores her daughter and I think it’s probably a good sign that we rarely hear about her and she’s living a relatively quiet life. My one negative comment: I’m sketched out by the age difference (21 versus 30 is a BIG deal) and by how much older Jamie Watson LOOKS. Also: Jamie and Jamie? And Jamie Lynn’s dad is named Jamie too. I just… can’t.

Her ring is simple and pretty:

Photos courtesy of Jamie Lynn’s Instagram.

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68 Responses to “Jamie Lynn Spears, 21, is engaged again, this time to Jamie Watson, 30”

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  1. Samigirl says:

    I know she’s an adult, and it’s only 9 years, but I just can’t help but be skeeved out by the age difference.

      • Emma - the JP Lover says:

        Well then, what will really creep you out is the fact that they’ve been dating for three years.

    • Erinn says:

      I was too… and in a way it is super skeevy.

      But at the same time, I think it might have been a good move. Not many men her age are ready to settle down and take on the responsibility of raising a child that isn’t their own. Hell, many don’t want a hand in raising their own child. Maybe this guys just in the same place in his life as she wants to be. And if that’s the case, it makes sense for her. Still a little skeevy, but at least it makes sense.

      • Me says:

        In a few years, no one will even notice their age difference. She is a single mom, not your typical 21 year old. Good for her finding a man to build a family with for her daughter.

      • mebee says:

        +1. Everyone’s a consenting adult here and I’ve seen way skeevier age differences and pairings. The guy seems to want to do right by her and marry her and help raise her kid. I don’t see a problem here.

    • TQB says:

      I don’t know – under normal circumstances, yes, it’s a big gap. But a 21 year old parent of a 5 year old is much different than a typical American 21 year old. She’s not off at college doing keg stands. She’s a mom, and from everything we’ve seen since she had the kid, that’s her priority. She doesn’t seem inclined to go back to showbiz. Maybe this guy is exactly her speed.

      • Tiffany says:

        I felt the same way. At first I was like, 21 is too young to be engaged! But since she has a 5 year old child, it makes sense that she would want to get a father-figure in the child’s life (though the real father should still be involved!).

        I can not imagine having been engaged twice, with a 5 year old child at 21. I was at a very great place in my life then: some responsibility mixed in with a TON of irresponsible fun. I feel sad for her for what she never got to have.

      • Pandy says:

        Isn’t she trying to get a country singing career going in Nashville? This one hasn’t been hiding under a rock in the sticks .. I highly doubt that.

    • energydrink says:

      There types of comments make me sad.. I’ve met my husband when I was 18 and he was 27. We moved in with each other within a week of dating, worked at the same company too(co-workers), so pretty much spent all our time together, and after 6 years we are still happy and feel “in love”, and act as each other’s rocks when life tries to bring us down.

      I know its the exception rather than the rule, but stories like this do exists, so maybe we shouldn’t be so quick to judge.

    • Jill says:

      I started dating my boyfriend when I was 20 and he was 30. We’ve been together for 12 years now, so sometimes an age difference doesn’t really mean anything.

  2. brin says:

    Congrats! Monogram towels will be a snap for them.

  3. Meredith says:

    The age difference isn’t such a big deal when you think Jamie Lynn’s been living an adult’s life since her daughter was born. Maturity-wise she’s closer to mid-20′s.

  4. Jayna says:

    Seriously? The girl is twenty-one, been a hand-on mother for four years. The last thing she needs is a boy. She needs a man with maturity and a good job. Marry some 25 isn’t necessarily the answer. Look at Ashlee Simpson and Pete. It didn’t last even though closer in age. It’s just that will she hit 30 after being a young mom for so long (probably a second one by then) and want to relive her younger years and party?

  5. Blue says:

    Ya, I was dating a 30 year old when I was 21. I was already ready to settle down but he wasn’t. They are probably on the same page so it could work, but I’m more creeped out by all the Jamies

    • Nina W says:

      I was engaged to a 32 year old when I was 21. It didn’t work out but she knows this guy after three years, it seems like a good fit for her.

  6. Mia 4S says:

    I really am side-eyeing the fact that this girl is still treated as a public figure. If she wanted to keep the kid she did the right thing moving home to a quieter life. Anytime I hear news about her now it seems…wrong.

    Well at least she’s a good cautionary tale. Birth control pills and condoms; they could be the difference between the Hollywood stardom you crave or getting stuck in your tiny hometown. Seriously, there should be a poster.

    • DeltaJuliet says:

      Well, she did post it on Twitter so…….

      • Mia 4S says:

        That’s very true DeltaJuliet, I have no doubt she still considers herself a celebrity. Which is incredibly sad.

        She ruined her shot in Hollywood (and yes I’m sure she loves her daughter) and there is an element of clinging to what she once had that is just awful to see in a 21 year old.

  7. Meow Mix says:

    So they started dating when she was how old?? Just Ewww.

  8. Nashville Girl says:

    She has actually been living in Nashville for the last several years. Maddie is in the same daycare as a friend’s kids and is supposedly delightful. JL is trying to break into the country music industry.

  9. dcypher1 says:

    9 years is not a big deal and shes 21 not 18. If the age difference was more than that it would be an issue. Their cool in my opinion. Congrats to them yay.

  10. Dana says:

    When i was 18 i dated a 29 yr old for almost a year and it was the healthiest relationship ive ever been in, and changed me from a selfish teenager into the FABULOUS woman i am today ;)

  11. Merritt says:

    “The Purity Myth” is a great book, the virginity obsessed are beyond creepy. Purity balls where you basically marry your dad are just ick.

    • Kate says:

      I am reading that right now and it is amazing and eye-opening.

    • j.eyre says:

      I think it is an important book and I hope it is widely read among everyone, not just women. Ms. Valenti’s arguments are well-supported and every time I worried should would go too far, she would give data to give proper credence for her statements.

      I have gotten 3 other people to read it, including my mother, and have recommended it to countless more.

  12. Syko says:

    I don’t see a problem here. She looks ecstatic, he looks like a nice guy. Once you are an adult, the years aren’t so important. My daughter, at 31, married a 22 year old guy. 18 years later they’re still married. No big deal.

  13. Cinnamon says:

    21 and 30 isnt that big of an age difference…. quite honestly, she’s had to grow up pretty fast and a regular 21 year old boy (because for the most part, they are still BOYS at that age) wouldn’t be the best fit for her anyway

  14. serena says:

    That’s true he looks old compared to her. He might be 30 but he does seems like 40. ugh..

  15. Jackie Jormp Jomp (formerly Zelda) says:

    That girl was 30 by the time she was 15, thanks to her parents. She’s seen a lot of life. I’d actually be troubled if she were seriously bonding with your average 21-year-old man.

  16. fabgrrl says:

    That is a rough looking 30! I would have pinned that guy as closer to 40, easily.

    • EmmaStoneWannabe says:

      Yeah..he kinda has a skeevy facial expression too..like, yeah, I’m getting with this..just, eww

  17. LadyJane says:

    I also think it is creepy when I see friend’s daughters on fb all dressed up to go out on a ‘date’ with their dad. Gross. Go out, fine, have dinner with your dad. But don’t call it a date. Just… ew.

    • Jackie Jormp Jomp (formerly Zelda) says:

      A man even being at all invested in his daughter’s virginity, in 2013, is f*cked. up.

  18. Anne says:

    I married my husband when I was 22, and he was 32, and we’ll be married 10 years in a few weeks, still going strong… I personally have hopes for the two of them!

  19. JL says:

    Who knows, the age doesn’t bother me as much as her upbringing.

    She’s been out of the spotlight and doing her own thing with her daughter for years so I’m hoping this is a good choice.

    She doesn’t seem to need his money, his name or a constant man in her life – so she may well be mature enough to decide wisely.

    I’m wishing them the best.

    • EmmaStoneWannabe says:

      “His money or name…”
      Who is this guy? Does he have a “name” or money??

      • JL says:

        I’ve never heard of him, I’m assuming he’s not famous, so it’s not like she’s with him for a tag along career boost.

        As for money, I don’t know but Jamie Lynn seems to have enough for herself and her daughter. He’s not mentioned in the media as “rich” so I’m guessing he makes good money but not enough to be a billionare “catch”.

        Just a regular guy, which fits with her low profile.

  20. judyjudy says:

    She’s a pretty girl. I’ve always like her.

  21. Cathy says:

    My parents had a ten year age different. As long as he makes her happy, that’s all that matters.

  22. CK says:

    Congrats to them! They look really happy.

    What’s the BIG DEAL with their age difference? I met my husband when I was 19 and he was 27. We’ve been together for 9 years, married for 3, have one awesome kid and another on the way. We have a wonderful relationship.

  23. Julie says:

    Gorgeous ring.

  24. SargassoSea says:

    Casey is so NOT the father of that baby. I thought this was public knowledge?!

  25. LadyBird83 says:

    She is most likely a very mature 21 year old. Having gone through everything she’s been through AND having seen her sis loose her mind. So congrats Jamie’s, you found love and peace in Nashville. It’s a great little big city.

  26. Jane says:

    Holy fucking cow. There is a a big difference mentally and emotionally being 21 compared to 30. So fucking creepy.

  27. PoliteTeaSipper says:

    Hopefully he’s a decent guy and they can have a happy relationship.

  28. RobN says:

    Congratulations and good luck. She seems like a very mature girl who has made very adult decisions and pulled them off very gracefully.

  29. lucy2 says:

    She’s still very young, but seems older and more mature. And at least they’ve been together a long time and not rushing into anything.
    She seems to be doing OK – I’d suspect getting out of the pressures of Hollywood was probably a good thing, regardless of the circumstances. I wish her sister would do the same and go to a place where she wouldn’t be so hounded.

  30. Pale fire says:

    I’m sorry but I’m watching my friend 27 date a girl for 4 months and get engaged w a girl 20. And it’s creepy. He’s all over her and controlling and it looks like his little sister. She’s over the moon I’m sure bc most guys at 20 are well immature. But so are we when were 20. There’s a WHOLE LOT of growing and changing in that decade. It seems sads to cap it and end it so young with a older dude. IDK that kinda creeps me out. I think you should go through your 20s and early 20s unattached having fun.

    • RobN says:

      Well, she’s got a five year old so the unattached ship has sailed. There’s also a big difference between four months and two or three years of being together.

      • Pale fire says:

        Def Robyn I agree. Jamie Lynn case is a little diff. I’m sure she’s lived a few lifetimes already growing up in her situation being on tv ect…my point was I think girls @ 20-21 have SO much living to do if you want to marry and settle down w a older more responsible guy wait at least till you’ve lived a little as a single adult enjoy it! I’m 27 and I couldn’t imagine getting married right out of college or in college. It’s when your finally breaking free from your parents control… Why go into a marriage w a guy who’s sowed his crazy oats when you haven’t … I dunno just my opinion. :)

  31. spinner says:

    In the first pic she looks like Ashley Simpson & in the 2nd pic she looks like Carrie Underwear.

  32. Alexa says:

    I wish her all the best. Congrats Jamie! I admire her grace in dealing with the challenging deck of cards she was dealt. Inspirational if you ask me!

    • fabgrrl says:

      Yeah, challenging deck of cards there — being too dumb, lazy, irresponsible or naive to use a condom.

  33. Patrice says:

    Yeah…This one gives me the creeps. I’m just about 30 and I no more have anything romantically/socially in common with 21 year old guys than I would a pair of sneakers! Yikes. The whole same name/he looks SO much older than her thing is giving me the major willies too. Maybe she was seeking out another father figure after her dad jetted of to CA to take care of Britney years back and her mother dropped her off in Louisiana once she was pregnant and no longer marketable :( Sad.

  34. shannon says:

    Everyone seems to think Jamie Lynn is trying to live a private life now. She’s not- she has been trying to make a country music career happen in Nashville lately, is what I”ve heard.

  35. Bridget says:

    Sometimes I think that baby was the best thing that could have happened to Jamie-Lynn Spears – she got out of LA and to what appears to be a ‘normal’ life in Louisiana, with apparently a pretty large chunk of money. She’s so lucky she didn’t get chewed up an spit out like Brit-Brit.

  36. Gena says:

    I can’t believe I am standing up for Jamie Lynn Spears, of ALL people, but I had to jump in and say that I was newly 21 when I got married to my husband, who was 31.

    I have always been a pretty mature person. My family were surprised but, then again, not very. I never was into partying and always kind of kept to myself and never dated. It wasn’t until *the* person came along that I moved in that direction… and it happened flawlessly and rather natural. It [us talking by chance/the evolution of our friendship] was over the internet, as well. (Dundundunnnn!) We didn’t say that we loved each other until we met in person, though… we were remaining reserved in case the ‘in person’ aspect did not work, but it did. First meeting off the plane and it was totally comfortable and lovely.

    I had never even LIVED with him prior to marrying him, either. In fact, we hung out in person for 2 weeks, then spent another 8 months apart, then spent another period of 2 weeks getting married and sorting out a spouse visa (he’s English.) I got up and moved away from everything I had ever known to the UK (I never visited before.) It was a big gamble but we figured, why not? It was that or spending thousands and thousands of dollars on going back and forth visiting each other… so we took a chance, but it’s been fine. He’s my best friend and my family love him like their own.

    We’re still married and I’m 27 and he’s 37. All is fine and well – no issues here!

    I think because she had a child so young, and she stepped up to it so responsibly and took her role as a new mother, from what I can tell, rather seriously–she’s probably a bit like I was… mature and in tune with herself. She probably has some sort of idea of what she wants out of life, with her daughter being a central part of that.

    Nothing about it bothers me at all… then again, I was the same age as her.

    Our minds seem to level out quite nicely with the age difference. I think if I was with someone similar to my age, there might be more moments where they would annoy me immensely… maybe not, but it works for me with this age difference. When we began talking it was never a factor, though.

    So, congratulations to her and best of luck.

  37. Jayna says:

    No one look at me. I was 21-and-half dating a 40-year-old playboy.

  38. Meg says:

    9 years isn’t bad, but 21 and 30 is huge because of how much you change in those years between 21 and 30