Meeting new people; why don’t guys ask me out?

Dear Guys,

When I know for a fact particular guys are interested in me, why are they so afraid to “break the ice” and talk to me? Is it the places I go? Gym, college, shopping mall, park. Are guys uncomfortable starting a conversation with a random person? Are they intimidated, have a significant other, or what could it be? As I mentioned they do seem interested. And I will also mention that I have approached a guy initially and it turned out he had a serious girlfriend. (He did tell me he found me attractive, but I still felt turned down and let down. I guess.)

So basically what should someone with my dilemma do?


Dear Sabrina,

Thanks for your question.

Well, meeting someone in a random place is always a crapshoot. A guy would have to have a whole lot of confidence to just randomly approach you at the mall, or even at the gym. And confidence aside, many guys just don’t operate this way. It’s too unpredictable. They have no idea who you are. (Although, meeting someone at college is a better possibility because you have common interests and goals.)

The other thought that comes to mind is, are you reading the cues correctly? Just because a guy smiles at you doesn’t mean he’s ready to ask you out. It could very well mean he finds you attractive, but it tells you nothing about his status—single or not. With this in mind you shouldn’t feel rejected from your encounter with the one guy. He was probably being honest with you. He found you attractive but he’s attached.

The thing is Sabrina, approaching guys at random places has a hint of desperation to it. (We’re not saying you are, but you might be perceived this way.) So we recommend you let the guys approach you. Then you’ll know for sure what their intentions are.

We also think you should try to meet guys more organically. (A guy in one of your classes. Maybe someone at the gym. Or at a college party. Maybe a friend of a friend.) Try to let things happen naturally. Don’t stress out about it. The more you focus on the things you love, the more likely you’ll meet people with similar interests, and then hopefully a spark will happen.

Please feel free to ask us a follow up question. And keep in touch and let us know how things are going. You also might be interested in our “Relationship Memoirs” page, especially Charlotte Pescale’s “Rebecca, a memoir.”


ps. Please let your friends know about us. Thanks! And please consider a small donation to THE GUYS. It does take time to answer questions thoughtfully and thoroughly. Use PayPal button on the right side of any page on our site.

Also check out:  Why is he not asking me out?  (There are a lot of comments/questions as well.)


5 Comments on Meeting new people; why don’t guys ask me out?

  1. Dear Guys,

    I have a similar concern to Sabrina’s about approaching strangers. I’m in college and a few weeks ago I was sitting in the hallway waiting for my class to start when I noticed this guy walking back and forth down the hall. After about the fifth time, I asked him if he needed help because he seemed lost. He explained his situation to me and said he didn’t think I could help but appreciated my concern. As he was talking to me, I noticed just how good-looking he was. I also deduced that he was pretty outgoing because he could have just said ‘yes’ or ‘no’ but he took the time to share his story with me. Anyway, that was that. I smiled and let it go.

    The thing is, I see him everywhere! So it’s hard to forget about him, and I always catch him watching me. I don’t know if it’s an “I think she’s pretty” look or a “hey that’s the girl that tried to help me” look. I always want to say something like, “Hey, I’m starting to see you everywhere”, but I don’t normally approach strangers and don’t want to be wrongly received. Plus, so much time has passed I feel like it’ll just get weirder the longer I wait.

    So, what does it mean that he’s always looking at me? And should I approach him? If so, how? I’m social, but somewhat insecure. I’m average looking, and he’s a 10.


  2. @Dani…..We understand your hesitation. Most people feel a bit unsure when approaching a stranger; even the so called “10s” can feel this way. His look could mean just what you said. 1. He’s interested and thinks your cute. 2. He remembers that you were nice to him and doesn’t know how to approach you to chat. But this is the perfect situation to go up to him and say hi. You’ve already kind of met him so why not just go up and ask him how he’s been? Remind him that you met. Is he a freshman? Maybe see how his classes are going. Sure it’s a risk, but it’s no big deal even if it feels that way. After that, let him initiate contact with you; that way you’ll know if he thinks you’re just someone nice or someone he’s interested in. What do you think?

  3. Hi, I have a similar issue. I have been taking guitar lessons for a few months and have found myself completely infatuated with my instructor. There is a kindness about him that I’m quite drawn to and he’s a very talented musician. He is also a bit younger than me. He’s 22 or 23 and I’m 30 (which doesn’t bother me at all). However, I’m unsure to tell him how I feel because I run the risk of rejection and having to find another instructor. I really don’t want to find another instructor as he’s quite talented and I enjoy learning the guitar. He has become the best and worst part of my week. It is great to see him and learn music, but then I have to leave him and try to spend the next week forgetting about him when in truth I want more. Sometimes I feel like he’s interested, but I can’t tell. We have a lot of things in common ranging from sports to music. Once I had sent him an email asking if he wanted to hang out with me and a group of friends at a local band concert. It was about a day before I heard back from him and he thanked me for the invitation and said that he was actually playing a show up in Lexington. I didn’t mention the show or email at all to him the next time I saw him. This response leads me to believe that he’s not interested. I don’t know if I should tell him how I feel the next time I have my lesson or just leave it alone. However, I’m consumed by thoughts of him and truly want to be with him. If he doesn’t want me then I need to move on and learn to forget him. It is getting too difficult to see him every week and not having it be more than just guitar lessons.

  4. @Sarah…..We understand your dilemma. It sounds like you’re going to need to say something to him. (You can always find another teacher.) We get the sense it’s going to be torture to keep taking lessons from him and feel the way you do. Worst case scenario: You say something and he politely rejects you and then you stop taking lessons from him. Best case: He’s into you as well. Of course, we kind of agree with your assessment. Based on his reaction to your invitation it sounds like he wants to keep this on a platonic level. But if this is going to drive you crazy, and if you’re going to regret not saying anything, then maybe you’re going to have to take the risk and let him know how you feel. What do you think? What’s your plan? Any other questions? Ask away and definitely keep us posted. ps. We hope you’ll share our site with all of your friends. Thanks. We appreciate it.

  5. Thanks for advice. I think I’m not going to say anything to him right now. Maybe I’ll wait a bit as I always seem to have a difficult time deciphering if guys like me or not. I’m trying to be more pragmatic and keep telling myself what I’m feeling is all in my head. I’ve just never felt so strongly about another guy before. I get butterflies in my stomach and feel lightheaded when I see him. I feel like it’s going to be torture to speak up and I do fear rejection. I also don’t want to be too forward. Is there something I could casually say to imply that I’m interested in him or are there signs I can look for to know if he’s interested in me? I would want him to take the opportunity to speak up first. I do try to complement him as much as possible by saying “you make playing the guitar effortless,” etc… as a way to make him feel good about himself. I also tried to go out on other dates to see if I could forget about him and meet new people. However, I found myself constantly comparing him to other guys I’ve dated. Clearly what I want and the reality of the situation are two different things.

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