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Thread: How should I handle this situation with shy guy I like?

  1. #1

    How should I handle this situation with shy guy I like?

    There is a man who works in the same building as I do, on the same floor as I do, at the opposite end of the hall from me. I have caught him looking at me many, many times since Christmas. When I tried to flirt back, I got just the opposite of what I thought I would: he wouldn't look at me, was frozen stiff in the elevator with me, and then took off in the opposite direction of where he needed to go just to avoid being near me. So I wondered if I was reading it wrong and he really hated me. Then I started doing my research and found out that shy guys push people away when they attempt to get close.

    Recently, his boss confirmed that he does have a crush on me, which I already knew deep down. So I have been trying to figure out what to do, because my situation is different than working with him or going to school or having mutual friends. We basically have none of that and the only way I ever see him is to run into him in the hallway of our office building. I am in my 40s and haven't had a relationship for years but want one. He looks to be late 30s early 40s. He used to play competetive sports at the semi pro level so I would think he would be accustomed to women hitting on him but maybe I'm wrong. He is VERY shy because he has only looked me in the eye once (after I asked his boss how I would ever get to know him if he couldn't look me in the eye.) Since then, he hasn't looked at me again, but I have upped my game anyway. I said, "Hi (his name), how are you?" and he said, "Good, how are you?" but never stopped walking so he was behind a wall by the time he spoke. Then 3 days later, he was dressed nice and I walked by him and said, "Wow, you look nice today." He kept walking, and it was about 3 more steps before he replied, "Thank you."

    I know what I am up against...and I still want to try. Since I hardly ever see him, how do I get him comfortable with me if I can only see him a couple times a week? I was thinking of leaving a note on his car but concerned that would be creepy. I could go in early and catch him in the hallway before he gets to work and offer him my phone number but would he use it? I could ask for his as well but would he give it? I could randomly ask when we're in the hallway if he likes mini golf (or whatever) and ask if he wants to go this weekend? I'm afraid of moving too fast and scaring him away but these "hi"s in the hallway may get old and take forever to progress. Or will they?

    Shy guys - what would you want me to do if it were you in this situation? Also, do most of you really want a relationship and love but are too insecure to try for one or are most of you satisfied with being alone? I can't imagine someone is living a full life if they are only admiring from afar and running in the opposite direction of love. BUT, I don't want to make any assumptions about what happens in other people's heads. Some insight would help.

  2. #2
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    My husband and I worked for the same company when we first met and he was incredibly shy at that time. He finally got up the courage to ask me out because he said I touched his arm while I was talking to him at a work event (which I really didn't remember doing!). I don't think most guys are too insecure to ask a woman out on a date and I don't think most guys are satisfied with being alone if they really want a relationship. Same as most women. Based on your comments my sense is that he was interested in flirting with you or checking you out and is not so much anymore -who knows why -maybe he changed his mind, met someone, etc. I would simply ask him, the next time you run into him, if he wants to grab lunch sometime. If he is interested and available he will jump at the chance. I think it's fine even though you really don't know each other -it's just lunch.

  3. #3
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    Well, there's being shy and being petrified of social situations, which is the way you've described it. Baya33 has a good suggestion. I would suggest you see if you can get his email address or company chat ID and chat him up. You can often reach shy people via the Internet or company network. You can ask him where he likes to have lunch or what he likes to eat, and the suggest you treat him to lunch. You can then suggest a second lunch if he goes for it, but make sure he pays.

  4. #4
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    I am that shy guy! I am also very self conscious. You could be forward and say, "hey John, when are you going to ask me out." He would then know that you are interested and that will give him the confidence he needs to "initiate", if you can call it that. Or you could tell his boss to tell him that he should ask you out, if he and his boss have that kind of relationship. Or, ask him if he has seen a new movie, and say you don't like watching movies alone, but you don't have anyone that wants to go with you. I think those would make it abundantly clear that you want to go with him.

    Your flirting may not be seen by him, if he is like me, I just think that is the way you are with everyone, so maybe a "I feel so open with you" or "I feel like you understand me", or "I'm never like this" let him know it is him, not just you're like that with everyone.

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  6. #5
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    I would absolutely not get his boss involved any more than he is right now because itís his workplace. I think emailing is fine but Iím not sure if he works for the same company- he may have strict company email rules where a personal conversation might not be appropriate. Iíd ask him in person and if he is that shy they he canít respond with a positive response - meaning even if he doesnít accept he follows up after now that he knows you are interested then you know he is not emotionally available to date you. I mean if itís his social issue that affect him to the point where he canít accept a lunch date with a woman he is really interested in then of course heís not going to be able to get to know you in any meaningful way.
    Iím typically not a fan of a woman asking a guy out in this situation as opposed to showing interest so that he asks her but since itís an unusual situation asking him to get lunch is sort of in the middle. I would not ask him when heís going to ask you out because itís a workplace and that really might give him the wrong idea and make him uncomfortable. It also suggests that you definitely are attracted where asking him to get lunch suggests itís not platonic but less of an in your face kind of way. When my husband asked me to lunch at work I genuinely wasnít totally sure if he was interested in that way Because we worked for the same company.

  7. #6
    Originally Posted by DanZee
    Well, there's being shy and being petrified of social situations, which is the way you've described it.
    YES! Petrified describes it well!

  8. #7
    One thing I may not have made clear is that we may work in the same building but it's not the same company so chatting or emailing isn't an option, unless he gives it to me. I don't trust his boss because I think he may like me so I don't feel that he is going to be of help.

  9. #8
    So if I was forward like that you don't think that I'm going to scare him off? After the elevator and run around the block incident, I thought I better take it slower but now I"m wondering if I just need to bite the bullet and go for it.

  10. #9
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    Ok, well use your judgement here, but for me I lack the confidence to ask a woman out. Not sure if it's shyness, I am very shy, I don't like revealing much about myself, or if it's fear of rejection (working on these with my therapist currently)

    I do this terrible thing of distancing myself when I think someone likes me, to see if they "chase" me in order to see if they really like me or if it's my imagination, so maybe just continue the chase. Use his name and touch his arm.

  11. #10
    Originally Posted by LVSound
    Ok, well use your judgement here, but for me I lack the confidence to ask a woman out. Not sure if it's shyness, I am very shy, I don't like revealing much about myself, or if it's fear of rejection (working on these with my therapist currently)

    I do this terrible thing of distancing myself when I think someone likes me, to see if they "chase" me in order to see if they really like me or if it's my imagination, so maybe just continue the chase. Use his name and touch his arm.
    I really appreciate your insight and I'm so sorry that this is the way it is for you. I hope that things get better!! 3 months ago, I had no idea that this is how some people were affected by shyness. It has been very enlightening and I like being able to put myself in their shoes to understand this better. I will definitely take your advice to continue the chase and hopefully he can ease up a little with me. He's probably wondering I haven't bailed yet!! But I'm not like most women so I think that we could be a good fit. Thanks.

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