John Mayer tried to pick up pop star by texting “let me tuck you in”

one splendid evening 2 270309

Just in case we didn’t have enough evidence that John Mayer’s a player, here’s another anecdote to put in his file. A few years ago Mayer saw 21-year-old pop country singer Jessie James at a restaurant in New York City. Though he was surrounded by women at his table, he sent someone over to get her to go back with him to his hotel room – along with all the other women. Throughout the night he hit on James, but without much luck. By the end he was left with nothing more than text messages, telling her he wanted to tuck her in.

John Mayer once tried to pick up pop starlet Jessie James by text-messaging her, “Let me tuck you in.”

James told “Boomer & Craig” on WFAN Sports Radio that she met the singer-songwriter in Manhattan.

“He had someone send for me [from] across the room,” James related. “He had a bunch of girls with him and he said, ‘We should [all] go back to my apartment.’ ”

She said Mayer left first to avoid the paparazzi, and when they got to Mayer’s apartment, “We were all hanging out and everyone started to gradually leave. It was just he and I at this point. I told him, ‘I need some taxi money, I’m gonna go home now.’ ”

Mayer asked James for her number and she gave it to him before leaving.

She recalled, “He texted me throughout the entire night while I was at the hotel room,” leaving messages like, “Let me tuck you in. I want to see you.”

While the show’s hosts labeled Mayer “a douche,” a friend of his shrugged it off, “He met her two years ago, it was not a big deal.”

[From Fox News]

Though I’ll take just about any opportunity I can to make fun of John Mayer, I really don’t think this story is all that bad. At least for Mayer. The only way I find it excessively creepy is that he was surrounded by lots of women. Somehow I imagine he kept hitting on them and as each one dropped off, he moved on to the next. And texting her throughout the night, even though she was in the room, is pretty lame. Something tells me that even though he’s famous – and I’m not going to lie, he’s nice to look at, as long as he doesn’t talk – he doesn’t have the easiest time getting some. I’m sure it’s simpler for Mayer than most guys, but part of me thinks he’s so over-the-top because he strikes out a lot.

He probably ends up with a girl whenever he wants, but I’m guessing he hits on ten a night that turn him down. Those aren’t great odds.

Here’s John Mayer at ‘One Splendid Evening’ sponsored by Carnival Cruise Lines and benefiting VH1 Save The Music Foundation held at Port Of Los Angeles on March 26th. Images thanks to WENN .

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21 Responses to “John Mayer tried to pick up pop star by texting “let me tuck you in””

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  1. stewie says:

    or maybe he strikes out a lot because he’s so over the top.

    or maybe most women know that he IS a douche.

    I think he expects women to fawn over him because he’s a pop star and, if they don’t, he steps up his pursuit a notch. or two.

  2. mae says:

    Pop “star” is a little excessive. “Pop “no one you’ve ever heard of” might work.

  3. MeowBea says:


  4. CandyKay says:

    I got that line too once! “Let me kiss you to sleep,” was the version I got. It didn’t work with me, either.

  5. Jeane says:

    “I told him, ‘I need some taxi money, I’m gonna go home now.’”

    She asked him for taxi money? Who does that??

  6. cherry says:

    Sounds like the start of a nightmare. He creeps me out in every way. How Jen could have dated him makes me totally lose respect for her. Ewwwwww

  7. Boom says:

    Is it true John Mayer used to be really overweight? like 400 lbs big? Maybe he’s just catching up on a lotta lost times with the ladies? – i still think he’s a jerk. he can use some class

  8. Embee says:

    I hate admitting this but I think he’s probably a great lover. He has such a soft-looking mouth…edible. And even if it is an act I bet he’s romantic and gentle in bed. I far prefer such an “act”over the guys who think that good sex is measured by how many times they can thrust in a 20 second interval. I hate that.

  9. orion70 says:

    “let me tuck you in” has a rather high ick factor….and is something that is said to little girls, not adult women. ick ick ick.

  10. Rosa says:

    What a pathetic douche bag…yuck.
    I agree with Cherry how can Jen have every had any thing to do with this loser it makes me think she is a loser to.

    To Embee you got the wrong idea-how about the satisfy him self and you get your self off kind of guy. You can tell by how little he cares for women.

  11. DiMi says:

    gross, pedofilic come-on

  12. lisa says:

    LOL, she asked him for taxi money.

  13. PJ says:

    He seems to be operating on the principle that if you ask enough women to go to bed with you, one of them eventually is going to say ‘yes.’ It works.

  14. Bodhi says:

    Eww! That massively creeps me out! And I know that women think he is good looking, but I just don’t see it. I think that, in another life, he would be driving a windowless van

  15. Katharine Jaynes says:

    LOL Jean! Taxi Money!

  16. SixxKitty says:

    eww, the slime ball keeps getting more and more disgusting…

  17. Pufft says:

    This post should read ‘country singer asks John Mayer taxi money’ – as that is a far more amusing and entertaining angle than the text messaging itself.

    Plus, what girl gives her number to a guy she has ZERO interest in? Well, apparently Jessie James (who the hell is she?) does. I’ve been known to give a ‘fake’ number just to appear polite, but giving my actualy number to someone I don’t particularly care for has and never will happen. I take it the pop starlet was a little star-struck and enjoying the attention. Why else go back to his apartment?

    Although I’m not a JM fan, but rather a fan of his music, I will continue to insist that this guy is simply misunderstood. I agree with Embee in sorts. He just needs to find a woman that understands him on every level (I’m sure this task in itself is near impossible as I always picture JM as a repressed artist with too many ideas in his head).

  18. Embee says:

    Rosa–You may be right, but I’m sticking with my version for now 🙂 A girl needs to have hope!

    Pufft–love your article heading!

  19. Jenna says:

    Jessie James went to my high school for her senior year. Warner Robins High School in Georgia. People are saying that she’s going to be a star because she’s willing to be the ‘bad girl of country’. Personally I’d like to see her stay the whole ‘No one has ever heard of you’ but she’s willing to show some skin with her dusty bushy eyebrows. But hey, if Mayer wants her then that’s great. Two douche bags together!

  20. Ted says:

    John and Jennifer Aniston two douche bags that belong together. Jennifer made the right choice in picking John Mayer.

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