Jennifer Love Hewitt sent Matt Damon a bed in the late 90s and he ignored her

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This is one of the more cringe-worthy stories I’ve heard, but nobody beats Jennifer Love Hewitt when it comes to self deprecating dating stories. Jennifer was a guest on the Jimmy Kimmel show last night. She told Jimmy that her 10 month-old daughter, Autumn, is walking already and she gushed about her like a proud, happy mom. She also praised her husband, Brian Hallisay, for being great with her during the birthing process. After that she told a story about how she sent a bed to Matt Damon through the mail and never got a “thank you” card from him. She really did this. Hewitt explained that she was just 20 years old (that would have been 1999), that it was in the post-Good Will Hunting phase, and that Damon had complained in an interview that he was traveling so much that he didn’t feel like he had his own bed to come home to. Hewitt took him literally and sent him an Aerobed to Paris, a move she now realizes was somewhat dumb.

“I was reading an article and he said this really sad thing about how all his dreams were coming true but he didn’t feel that he had a bed of his own, he was always traveling.”

“I remember being really busy also and thinking that’s so sad, to have all your dreams come true but not have a solid foundation. So for some reason, I though an aerobed would help that for him,” she admitted, laughing.

“In my head, I thought, ‘He can travel with it, then it’s always his safe place.’ I didn’t go over it with anyone, I should’ve been like, ‘Hey, should I send this to Matt Damon?’ and they would’ve been like, ‘No you’re crazy, don’t do it!’ But I didn’t, so I got the information he was in Paris, filming something, so I sent it to Paris.”

Sadly for Hewitt, the gift didn’t appear to go down well with Damon. “I never got a ‘thank you,’” she admitted. “It made me sad. I understand maybe his security never gave it to him, that’s a possibility.”

[From US Magazine]

Kimmel, who has a long history with Damon, said “you know why you didn’t get a thank you? Because he’s a creep. He’s got no class. What kind of person doesn’t thank another person for not sending them a bad.” Hewitt said “It made me sad in my heart.” Aww, she’s always chasing guys and getting rebuffed. Even though she’s married now with a little girl she’s still telling us about it because her foibles make for good stories. She knows this, the beautiful famous woman who could be a case study for “He’s Just Not That Into You.” I jest, I like J.Love and her silly stories of lost love. She might have been able to hook Damon with a little more finesse. Sending a dude a bed is in no way subtle.

Here’s J.Love telling the story of how she sent Matt Damon a bed:

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Jennifer Love Hewitt is shown at a CBS event in July. She’s joined the cast of Criminal Minds, which premieres on Wednesday. Credit: WENN.com

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59 Responses to “Jennifer Love Hewitt sent Matt Damon a bed in the late 90s and he ignored her”

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  1. Jaderu says:

    Damon never thanked me for the knitted Ben Cozy I made and sent him either. I wanted him to be able to keep his Ben warm and in a safe place.
    Oh well Matty. I tried.
    Ingrate.

  2. Abbott says:

    You should’ve just named an album after him like a normal stalker.

  3. Charlotte says:

    She’s so perky and pretty and has a killer rack. I guess she really must be high maintenance to seem to have such bad luck. She always strikes me as being in need of a ‘girl, please’ friend. If she’d listen, that is.

    • Christo says:

      The problem is that she is too self-involved to have any real girlfriends. In addition, her wandering eye would make any potential female friend wary of her at the onset. She must have good connections, though, because she always seems to land a television show. Someone or, rather, some man at CBS obviously likes her because the opportunities find her time and time again.

    • QQ says:

      I don’t know that she’d listen to a “Gorl..Please STOP” friend..she is so damned cringeworthy and pressed!!

      • Charlotte says:

        Yeah…. That papp-friendly Breakfast At Tiffany’s thirtieth she threw herself. I guess any real girl friends have given up. And the others probably enjoy watching ringside.

    • Isabelle says:

      Matt Damon never seemed to be the manwhore type, he seemed to be a relationship kind of guy. He was on the tamer side of dating even during his single days. JLH would have been too much for him.

    • Ivy says:

      I think she’s really sweet but probably the type to get bored after a month of dating.

      Sending the bed was a really dumb idea. Why do that? That’s really creepy.

  4. Sugar says:

    Yikes! That jump suit gives her the figure of a Teletubbie.

    • Jaderu says:

      Talk about Yikes. She just had a baby. Give her a break.

      • sienna says:

        She didn’t say she has a bad body, just that the jumpsuit is unflattering…. which it is.

        Besides she didn’t just have a baby, in the interview she says the baby is 10 mos old.

      • Jaderu says:

        Oh okay. Right. I forgot women are supposed to be back to their pre-baby weight before 10 months. Ok. Gotcha.

      • Sugar says:

        I didn’t say her body was bad. Read my comment again. I simply pointed out that the jumpsuit is wickedly unflattering.

        She didn’t just have a baby, either.

    • Erinn says:

      I agree, Sugar – it’s not a flattering outfit at all. I’ve seen her in cuter things post baby. But she’s always had a hard time with flattering her figure, so eh. I like the colors for her, but it does something weird with her bust and her hips. It makes her look larger than she is, and I think the pattern along the bust is partially to blame.

    • Jag says:

      She’s beautiful, but that outfit has to go! I like her hair longer, too, but with a wee one, short like that is probably best.

  5. Paloma says:

    I would have never admitted this.

  6. pretty says:

    just googled Matt Damon 1999 and drooled all over looking at the photos. he was reallllly hot, wasn’t he?

    • DarkSparkle says:

      Yes, yes a thousand times yes. Dogma for the win. So, so hot.

      School Ties is also great, but his hotness (and that of Brendan Fraser) was overwhelmed by such a serious, intense movie.

  7. Rose says:

    That outfit is really unflattering to her. Emphasizes the hips, which is what she should be avoiding. I don’t think she ever would have had a chance with Damon, if that was what she was hoping for. Not quite ever in his league. Wasn’t he dating Minnie Driver in those days, before he dumped her for Winona? I still like Jennifer, she seems down to the earth and I like the self deprecating stories.

    • Rhiley says:

      My feet are screaming at me for looking at those shoes. “Don’t you EVER try to squeeze us into those, ya hear?”

  8. Kiki says:

    I am lost. What is Kimmel’s problem with Matt Damon?

    • Sara says:

      its a running gag. i dont follow Kimmel so i dont know if they still do it or how long it went on. but it was often that Matt was introduced as a guest but they never had time to get him on the air or he got out, sat down and then they realized they had no time. Matt then was shown acting angry about it.

      Kimmel used to date Sarah Silverman and she did a song called “im f*cking Matt Damon” featuring Matt Damon, Kimmel countered with “Im f*cking Ben Affleck” featuring Ben Affleck.
      should be on youtube.

      • FLORC says:

        hah! I was going to ask the same. It’s hard to tell what is a bit and what is real with him. Remember twerk girl? Yea.
        Affleck getting in on that sort of thing makes me think it’s a bit. I doubt he’d do that if it was really to nurture hatred of Damon with Kimmel.

      • Bella bella says:

        @Florc, It’s definitely a bit. It’s been a running joke between Jimmy and Matt for years. The show is always just unfortunately ending when Damon comes out, so they don’t have time for him to be a guest. Then Sarah did her song/video, which is hilarious. Then Kimmel did his retort. And THEN, I think it was for Kimmel’s first show of the season, or maybe the last show of the season, or maybe Kimmel got sick, but Matt Damon hosted the show. (After all that time with there never being enough time for him to talk.) And he had all these incredible “A”-list guests/friends on the show, the kind of people Kimmel joked he could never get to come on the show. (I don’t know — I don’t watch him but I did see the Matt Damon night.) It was funny.

        So this is just a continuation of their very funny jabs at each other. And if you have never seen Sarah’s video “I’m f*cking Matt Damon”, you should check it out. It always makes me laugh.

  9. Dani2 says:

    I’m just so embarrassed for her, I don’t know why a person would volunteer information about something so embarrassing that happened nearly twenty ages, there was no need.

    • FingerBinger says:

      This story isn’t embarrassing. It’s actually kind of funny.

      • Charlotte says:

        Yeah, I think largely she’s adorable and self-deprecating, which is how I found this story. Which, again, really makes me wonder at those stories of how much work she is.
        I love that she shared this. So funny.

      • Dani2 says:

        Well I never said you had to agree with me lol, different people get embarrassed by different things, for me, this is the height of embarrassing.

      • FLORC says:

        I have loads of embarrassing/funny stories from dating and being young. Some might swing between shame and hilarity. That she can laugh at herself and make us laugh is great. All those stories could be painfully embarrassing without her approach to them and sharing for a laugh. Lord knows she’s got plenty to tell!

        Although, that 1piece she’s wearing and the pantyhose over her feet in sandals is terrible. Still love her!

  10. aims says:

    Her outfit is horrendous.

    Secondly, that was really a stupid thing to do. But I believe if anyone would do such a drastic look at me thing, it would be Jennifer.

    • FLORC says:

      I think you’re only seeing the bad and a chance to attack. Not 1 of us here can say we haven’t done something silly like that. MAybe not involving international shipments, but the same misinterpretations of people we liked.

    • Bella bella says:

      Can you imagine how embarrassing it must have been? If it were me, I’d be making jokes about it, too. I can think of at least a few times when I behaved in a ridiculously inappropriate way to a guy that I was crushing on.

  11. HappyMom says:

    I’ve always had a soft spot for her-she’s kind of a loon, but she doesn’t seem malicious. But she looks horrendous in these pictures-her outfit, her hair, the multiple earrings-yikes!

  12. Ag says:

    oh, god, she’s back with her cringe-worthy stories. girl, leave it all in the past, don’t volunteer ANY of this information.

  13. Talie says:

    I can’t believe she actually said this out loud…

  14. Green Is Good says:

    Some confessions should never see the light of day. This is one of them.

  15. TheCountess says:

    Wow, I always though the rumors about her being desperate were exaggerated. How embarrassing.

  16. lucy2 says:

    She is a bit of a wackadoo, isn’t she? She seems sweet and all, but I’ve never seen someone so openly desperate – though it seems marriage and motherhood have helped her grow beyond that (I hope.)

  17. here's Wilson says:

    Enjoyed! I find self deprecating humor to be good for the soul. . Use it all the time!

  18. Size Does Matter says:

    Is it just me or is she unrecognizable in the video and stills from the video? But she looks like herself in the regular photos.

  19. Penelope says:

    Just to get it out of the way: Her outfit is terribly unflattering. What a dreadful fashion choice!

    That said, I’ve always liked Jennifer–her unforced, unaffected sweetness always seems to shine through. She seems more “real” than most of the Hollywood crowd.

  20. Irishserra says:

    She looks like Jennifer Gray in that header photo.

    • Denise says:

      Thank you for saying that! I thought that immediately and couldn’t believe the thread wasn’t flooded with that comment!

      The jumpsuit, I think I know what happened. She was a lot bigger before, lost some baby weight and in her optimistic mind she sees what’s not there instead of what’s still there. I think that’s happened to most of us. I’ll bet she thought the jumpsuit looked good when she tried it on and she went with it. But a sleeveless top is tough as it is, never mind the way it cuts in, you need to be super toned to pull that off. It’s nice that she had the confidence to wear it though. She seems happy.

  21. Miss M says:

    Bless her heart

  22. JenniferJustice says:

    “…perhaps his security never gave it to him.” Or perhaps they did and it totally freaked him the f–k out!

    • Bella bella says:

      I think it’s quite possible that the people around him decided he didn’t need to see the air mattress. Or whatever it was. I’ve been in the position of being a screener of the stuff that comes from strangers to a well-known person, and people send some weird stuff!!

  23. anne_000 says:

    She’s crazy and I like that she knows she’s crazy and admits to it.

    I think she’s put too much botox or whatever in her forehead. She looks better when her face is more natural.

  24. AliV says:

    Rich Cronin gave a great interview on Stern how incredibly in love he was with her. They started dating and she eventually gave him a promise ring to signify their commitment. Dude later found out she gave a bunch of those rings to other guys she was dating at the same time as him.

    I recommend anyone listen to the interview. He said she also wanted him to put on two condoms the first time they had sex. But he doesn’t ever badmouth her just describes her craziness. He really loved her.

  25. Str8Shooter says:

    OMG! That first pic looks like Ann Coulter with a brunette wig!!