I (36F) went on a boat tour yesterday for a team-building event as my fully remote team got together for a few days. One of our guides was super handsome, funny, and we had a lot in common as we were from the same city. He played music and I know my local rap artists and we shared a smile over a classic rap song that is an anthem to my local city. I wasn’t in the clouds and thinking we had some love connection, but it was cool to have something in common with someone. I am super shy, and trying to meet people in the wild as scary as it is. But I really felt like I should not let this encounter slip away so quickly.

My colleagues all told me to ask him for his number but I am way too shy for that but my colleague had his work cell still in her recent texts, as they had coordinated the tour together. She text him asking if he was single (with my approval) and told him someone on the tour was interested. He asked who it was and we didn’t know what to say so I told her to send 2 pictures of me, and let him know I thought he was cute, and to include my number but to make it clear that no pressure at all to contact me..

That was at around 10 PM last night. I dont mind that I have not heard from him, but men, would this turn you off? I did not want to come across needy or desperado.. I just thought he was handsome and it was worth the risk..

31 comments
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  2. The turn off would be that you didn’t have the balls to just say something. You’re 36 and passing notes through your friend like a teenager.

  3. You’re an adult. Just act adulty. Go up to him and talk ro him. This texting things through friends is really silly and would annoy me.

  4. I’d be put off, you just introduced a whole audience into this. It would have been better to approach him or text him yourself.

  5. No, most men aren’t that complicated. If he thought you were attractive, he would be plenty turned on.

    Is it sexy that you didn’t muster up the courage to ask him out directly? No, and that would’ve increased your chances, most likely. But ultimately, if he liked your looks, none of that would’ve mattered.

    I hope this doesn’t make you feel badly about yourself and discourage you from asking people out. You’re playing a numbers game. But I recommend just being direct. What’s the worst that can happen?

  6. With how vanilla this approach is, I’m guessing the local song is by Marky Mark and Funky Bunch.

  7. Your friend screening whether he’s single without letting him know who “was interested” is just ridiculous. Girlfriend or not he’d want to know who it was.

    “I’m seeing someone” is one of least awkward ways of letting you know he’s not interested, whether it is true or not. Give him an out.

  8. Wouldn’t turn me off totally, but I’d probably think you were not in any way adventurous. I’d probably meet you and try to get to know you, but I’d probably want you to prove you are the kind of person I like, pretty soon

  9. An adult woman acting like a teenage girl? Yep, not interested.

    An adult woman willing to come up and talk to me? I’d probably say yes out of shear curiosity about her. Even if I didn’t find her attractive at first.

  10. A woman showing interest? I wouldn’t be turned off at all. If anything I view it as an entertaining way we met.

  11. My first thought would be that it’s some sort of trick or joke and I would most likely just ignore it. If I did respond I’d be very suspicious.

    As others have said It’s teenager stuff. I’m not interested in teenagers and their shenanigans. I can’t speak for that guy, but I wouldn’t be keen.

  12. Well, that doesn’t exactly scream “confident woman”. I appreciate when women are willing to once for a change take on the risk of rejection instead of me all the time, but I might consider this particular way to be a bit immature and yeah, perhaps a turn off, depends on more details tho, especially how attractive you are in the photos or if you somehow got his attention before.

  13. He’s a handsome tour guide, sweetheart. Women on tours handing him their numbers or trying to sleep with him the night of the tour are pretty common. You missed a chance for a hot romp, that’s it. Because even if he was way into you, last thing you need to fall in love with is a hot tour guide. Modern day cowboys.

  14. I don’t know. The guy is working. And now somebody is hitting on him. Probably not the greatest situation (if you flip the genders it would definitely not go down well… sigh). Unless you’re super hot, wouldn’t be surprising if he never texted.

  15. This would turn me on so much. Not in a sexual way, but in an “that’s awesome and definitely will call” way

  16. I mean if your friend had his number it would be better to text him yourself if you couldn’t find opportunity to talk to him in private..

  17. This was some straight up middle school behavior. Go up and ask the dude directly. The worst he can say is he’s taken or no. Trust me, guys are a lot nicer giving rejection than women are.

    As hard as it is for me to meet people being an introvert and not finding many shared interests, even I would be turned off by the behavior as it shows a lack of maturity, even if you weren’t the one that asked via text and sent pics, you still approved it.

  18. You’re 36? This post reads like you’re 16. Be an adult, and talk to the guy if you’re really interested.

  19. If the the gender was reversed you might have been called a creep by Reddit

  20. 36 and making your friends do the dirty work. smh.

    some guys might actually go for this, since it’s quant and kinda cute. if you’re 20.

    huge turnoff. this isn’t high school. learn to talk to someone like an adult.

    (and being from the same city doesn’t mean you “have a lot in common,” it means you have *one* tiny inconsequential thing in common.)

  21. The whole thing would make me think you’re children, and unless I were desperate at the time, I would definitely not engage with you

  22. No its not a turn off, but you definitely came across as shy. Your work friend didn’t do you any favors by being mysterious with the man. I understand that she was screening you for him so she could know if he was thinking about you too. I think the fact that he asked “who was it” is what’s making you feel this way, because “how could he not think it was me?”. He’s a tour guide and probably gets his fair share of attention as well. She could stand to be more direct with him. Playing games and being mysterious would turn us off especially if we have other options in terms of women.

    If you like us, just say it. Youre never desperate or thirsty or weird for expressing interest in someone. Just give them the opportunity to say yes or no.

  23. So many people being rude here. You’re shy and at a professional function so you didn’t get his number. Perfectly understandable. You both were working but could t connect but you’d like to. I think it’s fine for your friend to pass along your contact info. Don’t let an opportunity pass or you’ll always be thinking if it could have become something good.

  24. Expressing your interest is not needy or desperate. I wish more women were confident to make the first move, because we guys are stupid sometimes and don’t see signals and assume nothing is going on.

    But frankly as an adult, you should just ask his number yourself, thats a clear enough sign.

  25. With the context provided I’ll provide my thoughts:

    -Your 36 and approaching this like a junior high girl. My friend thinks you are cute teehee. It’s not cute. You messed up by getting your friend involved. You could have easily said something along the lines of “hey, I had a great time on this tour- I’m New to the city would you be interested in exchanging contact info, I feel like we had a a lot in common”.

    From his perspective he’s working, you contacted him on his work cell through a contact he does business with. He’s in a difficult situation now because there could be some ramifications back to his business if things don’t work out. He has a professional reputation to uphold. As a tour guide his literal job is to make sure that Patrons enjoy themselves. Definitely wouldn’t have been out of bounds to approach him one on one, but bringing others into it is weird.

    Your 36, you need to learn to have more independence and shoot your own shot. If he was interested, he’s probably thinking that you have no discretion and will tell your friends everything. Unless you are really attractive i don’t think he’s gonna reply.

  26. Hard to answer your question. If I were in his shoes, given your description, chances are I would be in a relationship already and receiving any text advances would be ignored to protect that relationship.

    Does that make any sense?

  27. Idk. In high school it would’ve been cute. In my 30s, it’d be a hard pass.

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