I’m not a fan of Chelsea Handler by any stretch and don’t find her funny, but I appreciate her willingness to dish on other celebrities and to tell details about her (often messed up) love life. Case in point: Chelsea was on Kristin Cavallari’s Let’s Be Honest podcast, where she dished about a bad first date with Bobby Flay. This story is convoluted but apparently she was staying at a hotel with some girlfriends and she was talking to Bobby on the phone. Bobby told her that he loved the hotel and would order room service for her. Only when the bill came Bobby had not covered it.
Do you have a bad celebrity date story that we don’t know about?
I went on a date with Bobby Flay that was pretty bad. He ordered me room service. So, we were talking on the phone, flirting a little bit. I was at at a hotel with some girlfriends and I think we were filming for Netflix. He’s like, “Let me order your food for you. I love that hotel.” He orders me food. He’s gonna love this. But then they brought me the bill and I’m like, “What is this guy?” And then
somebody was like, “Oh yeah, he’s really cheap. He’s really cheap.” I hate cheap. If you’re penurious, I’m not interested in you. I’m generous and I like people to be generous with their money. We did end up going on a date and it was just not a match.
That’s a very good use of the word “penurious.” You don’t hear that in regular conversation. The only excuse I could see for this was that it was logistically difficult for Bobby to pay the bill. Like the hotel automatically bills it to the room unless you insist they put it on your card and double check. Given everything we’ve heard about Bobby though, this tracks. I suspect that Chelsea and Bobby did more than just date one time considering that we heard about it back in 2016 when it happened.
EW has more details about Chelsea’s dating life. She’s apparently seeing a “Florida construction executive” if that’s even still happening. (Update: they’ve split already.) In a recent interview she described how they met:
“I had to ask this guy sitting at a blackjack table who was wearing a cowboy hat. He had a lot of chips, like, thousands of dollars,” Handler told the publication of their first interaction. “I was like, ‘Hey, buddy, can I borrow $1,000? I’m gonna start winning right away. And he was like, ‘Yeah, absolutely!’ So he gave me $1,000.”
Handler said she won “immediately” and paid him back, with interest. The next morning, she got a mysterious text that read, “I had so much fun with you last night,” only to learn that her friend had slipped Largura her number.
Get your daily dose of entertainment news, celebrity updates, and what to watch with our EW Dispatch newsletter.
Handler then invited him to join her on a vacation to Antarctica that she had already booked for Thanksgiving. “He bought a ticket and met me there,” she said.
The pair ended up ringing in her 52nd birthday [sic] together under the Northern Lights.
“I’m still going strong with this guy,” she said. “It’s hot, and a woman like me needs a big move like that.”
The story about Chelsea meeting a guy at a blackjack table and then borrowing $1,000 from him is not the meet cute she thinks it is. It’s red-flaggy that he went Antarctica with her right after that, but Chelsea is a walking red flag. He must either be rolling in it or deep in debt. In her Kristin Cavallari interview Chelsea said she doesn’t stay beyond six months in any relationship because she’s “not interested in your family or your issues” and that she doesn’t want to be part of a couple. She also compared dipping out of a relationship to leaving a party early or avoiding getting addicted to drugs. She cuts the guy off before she ends up needing him. That’s not my philosophy at all, but a lot of men in particular operate that way, they just don’t explain it that plainly.
Photos credit: Xavier Collin/Image Press Agency/Avalon, Sadou Faye/Avalon, M10S/TheNews2/Cover Images
Shes not wrong and she has her reasons for being like that. Many men see women as caregivers and se.x objects. The longer you date a guy, the more care they expect from you. The Mental load rises the longer the relationship goes for woman. Yeah, no thanks
This. Chelsea is doing what many men do as a default. Suddenly it’s a problem when a woman does it.
I am surprised that I recommend my separated/divorced/single friends not to get back into a traditional relationship when we talk about relationships at our middle age life. Have a boyfriend, do whatever activities you want to do together, have fun and then go home to your own house until next rendezvous. Dont deal with money issues, kids schedule, other people’s debt you have nothing to do with, etc, etc. I am a happily married woman with the same man since 30years+, but I am not doing this again with nobody else and by hearing the horror stories from my friends meeting people, I hear the market is full of dudes that are cheap, not gentlemans and behave poorly: example, coming over for dinner empty handed, not helping out before/after dinner, and watching tv instead of trying to help out. Wtf. the bar is so low it’s in hell. No thanks
I have never failed to be astonished at how much emotional / logistical / even physical labour men expect women to do for them, once they award you the status of being the missus. My husband actually asked me the other day at a children’s cricket match if I could put on his sun cream for him. I mean. LOL. Like, the kids were like, dude, really???
I’m not mad about her for any of it (except having anything to do with the asinine, arrogant Flay). I also admire how cool she plays it, investing little emotional energy.
sorry, “mad at her,” not “mad about her” I think I really need my second cup of coffee!
I love that she’s made the choice to put her needs and desires first.
this is survival under patriarchy.
Dating someone for that short amount of time just to terminate the relationship sounds exhausting, I would prefer not to date at all. But if it works for her, good for her.
ooshpick, Nice take!
At least she’s not lying haha.
I read her book years ago and she is genuinely funny in my opinion. I think it’s great that she wants to stay single, and I think that relationships really aren’t for everyone. I’m not even sure how my relationship happened because I was OVER dating and just refused to do it. Chelsea has big girl money that she earned herself and that buys the freedom to do whatever the hell she wants, and that’s exactly what she does. I love an independent woman.
Delphine, hear, hear.
So many articles I’m reading lately, in the past year really, that discuss middle age and older women not wanting to be in a serious relationship or live with a guy. I’m 52 and have not had a serious relationship in 7 years. It feels nice to know that I’m not alone in my thinking. I go on dates and am perfectly content with keeping it “light”. There have been a couple of times after dating a few (short) months, a couple of guys wanted to move in that direction. No Thank You! I’m not taking care of a man at this point or any point in the future.
Out of all the things in this article, it’s the incorrect statement of them having seen the NORTHERN lights in ANTARCTICA that stands out for me. Scientifically impossible to see the Northern Lights in Antarctica; maybe they meant the Southern Lights aka Aurora Australis, and that’s something that an outlet like EW could have — and should have — Googled.
Well, we’re talking about Chelsea Handler, the woman who legit thought that the moon and the sun were the same thing. Really. Not kidding. Until age 40, she thought it just set and rose up again in a different form. 😳