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


Decemberbrid

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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.

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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.

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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.

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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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I would absolutely not get his boss involved any more than he is right now because it’s his workplace. I think emailing is fine but I’m not sure if he works for the same company- he may have strict company email rules where a personal conversation might not be appropriate. I’d ask him in person and if he is that shy they he can’t respond with a positive response - meaning even if he doesn’t 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 it’s his social issue that affect him to the point where he can’t accept a lunch date with a woman he is really interested in then of course he’s not going to be able to get to know you in any meaningful way.

I’m 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 it’s an unusual situation asking him to get lunch is sort of in the middle. I would not ask him when he’s going to ask you out because it’s 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 it’s not platonic but less of an in your face kind of way. When my husband asked me to lunch at work I genuinely wasn’t totally sure if he was interested in that way Because we worked for the same company.

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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.

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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.

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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.

 

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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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.

 

I don’t thInk it’s forward or chasing him to ask him to lunch. If he is that petrified and that is why he is not asking you out then ask yourself if you will be ok doing most if not all of the initiating and keeping the conversation going. I personally wouldnt be. I’d at least need it equal. My better sense is that he’s just not interested in dating you even though he finds you attractive and or he met someone in the meanwhile. But it can’t hurt to ask him to lunch.

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I don’t thInk it’s forward or chasing him to ask him to lunch. If he is that petrified and that is why he is not asking you out then ask yourself if you will be ok doing most if not all of the initiating and keeping the conversation going. I personally wouldnt be. I’d at least need it equal. My better sense is that he’s just not interested in dating you even though he finds you attractive and or he met someone in the meanwhile. But it can’t hurt to ask him to lunch.

 

Yes, I have asked myself if I want a man who doesn't take on that role. It's a valid question. But this is why I came on this site; to get the perspective of a shy guy or girl; to understand why someone would want to admire from afar and never have the object of their desire. I'm pretty confident that he hasnt met anyone else as the conversation that I had with his boss was recent - indicating his crush. He wouldn't have stirred the pot they way he did if there wasn't some reason to.

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It is apparently pretty tough to date a shy guy, just ask my ex. I never asked her on dates and had a lot of trouble expressing my feelings, so much so that she didnt believe me. "Actions speak louder than words". What is your love language? I performed acts of kindness, but had trouble with words of affirmation, and physical touch.

 

I imagine if you finally date this.guy, he will be incredibly dedicated and create a long lasting relationship.

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Yes, I have asked myself if I want a man who doesn't take on that role. It's a valid question. But this is why I came on this site; to get the perspective of a shy guy or girl; to understand why someone would want to admire from afar and never have the object of their desire. I'm pretty confident that he hasnt met anyone else as the conversation that I had with his boss was recent - indicating his crush. He wouldn't have stirred the pot they way he did if there wasn't some reason to.

 

His boss may not know. It's a work environment not personal. And he might be dating someone at his work so he doesn't want the boss to know and is covering. My husband initiated after asking me out to lunch and despite being very shy. Because he was that into me. And I don't write that to "brag" just that even very shy people will step up to the plate if it's something he or she wants. Like all the shy people who excel at Toastmasters courses for public speaking because their dream job involves public speaking. For example. I don't agree that a shy person will be anymore dedicated as a partner than anyone else. Apples and oranges.

 

Yes, actions speak louder than words and if a person isn't willing to put in an equal effort in a relationship or a balanced/fair effort that can cause a host of problems. My husband came out of his shell as he got older -for specific reasons and not just years passing. And it was challenging at times to be in social situations with him and be annoyed that he wasn't making more of an effort -or any effort -to make conversation, especially when he was meeting my friends for the first time. But I changed too and worried far less about 'impressions" on others (which was a really good thing when I became a parent- that can do you in LOL - just an aside in case you are inclined that way).

 

So I would ask him to lunch and see how it goes -one step at a time. Just continue to be honest with yourself and to me it would be perfectly understandable if he doesn't reciprocate, show interest, step up to the plate, to determine that you're not someone who wishes to be the main pursuer, the main initiator, in a romantic relationship.

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Sorry to hear this. It's best to get on some dating apps and start chatting with and meeting interested men. Chasing this guy down and rationalizing it will lead to a self perpetuating cycle of "I am in my 40s and haven't had a relationship for years but want one".

 

Just because you have a crush on someone it does not mean he is interested or available. Rather than assume "he's shy", assume if he were interested you would know because he would have talked to you/asked you out months ago. Have you read the book "He's Just Not That Into You"?

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.
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It is apparently pretty tough to date a shy guy, just ask my ex. I never asked her on dates and had a lot of trouble expressing my feelings, so much so that she didnt believe me. "Actions speak louder than words". What is your love language? I performed acts of kindness, but had trouble with words of affirmation, and physical touch.

 

I imagine if you finally date this.guy, he will be incredibly dedicated and create a long lasting relationship.

 

That's why I am motivated to continue this - for the benefits it poses to both of us. Huge hurdle to get over first.

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That's why I am motivated to continue this - for the benefits it poses to both of us. Huge hurdle to get over first.

 

I wouldn't assume any benefits to him at this point -you are assuming he is very shy and that that is why he is not asking you out, you are assuming he told his boss the truth, etc. Only ask him out if you would like to have lunch with him and get to know him better as a person. I know it feels like a hurdle but really it's not -it's just lunch.

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His boss may not know. It's a work environment not personal. And he might be dating someone at his work so he doesn't want the boss to know and is covering.

 

 

 

So I would ask him to lunch and see how it goes -one step at a time. Just continue to be honest with yourself and to me it would be perfectly understandable if he doesn't reciprocate, show interest, step up to the plate, to determine that you're not someone who wishes to be the main pursuer, the main initiator, in a romantic relationship.

 

There are 4 people in his office and they are all men. They wear flip flops and shorts to work - not the typical environment.

 

Staying honest to myself is very important!! Thank you.

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There are 4 people in his office and they are all men. They wear flip flops and shorts to work - not the typical environment.

 

Staying honest to myself is very important!! Thank you.

 

I'm not sure what the relevance is of how the people in his office dress. It's still an office. It's how he earns his money (I think we can assume he's not going there for fun to work for free)

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His boss may not know. It's a work environment not personal. And he might be dating someone at his work so he doesn't want the boss to know and is covering. My husband initiated after asking me out to lunch and despite being very shy. Because he was that into me. And I don't write that to "brag" just that even very shy people will step up to the plate if it's something he or she wants. Like all the shy people who excel at Toastmasters courses for public speaking because their dream job involves public speaking. For example. I don't agree that a shy person will be anymore dedicated as a partner than anyone else. Apples and oranges.

 

Yes, actions speak louder than words and if a person isn't willing to put in an equal effort in a relationship or a balanced/fair effort that can cause a host of problems. My husband came out of his shell as he got older -for specific reasons and not just years passing. And it was challenging at times to be in social situations with him and be annoyed that he wasn't making more of an effort -or any effort -to make conversation, especially when he was meeting my friends for the first time. But I changed too and worried far less about 'impressions" on others (which was a really good thing when I became a parent- that can do you in LOL - just an aside in case you are inclined that way).

 

So I would ask him to lunch and see how it goes -one step at a time. Just continue to be honest with yourself and to me it would be perfectly understandable if he doesn't reciprocate, show interest, step up to the plate, to determine that you're not someone who wishes to be the main pursuer, the main initiator, in a romantic relationship.

 

I'm not sure what the relevance is of how the people in his office dress. It's still an office. It's how he earns his money (I think we can assume he's not going there for fun to work for free)

 

The relevance is that it is very relaxed and casual between them and I see the kind of relationship that they have. You haven't seen anything and frankly, your "devil's advocate" role is not helping anymore. Thank you for your contribution of "it's just lunch" , but it seems a little insensitive. It was just a "ride in the elevator" and he almost freaked out. I have valid concerns about coming across too forward yet. I know where you stand, thank you.

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The relevance is that it is very relaxed and casual between them and I see the kind of relationship that they have. You haven't seen anything and frankly, your "devil's advocate" role is not helping anymore. Thank you for your contribution of "it's just lunch" , but it seems a little insensitive. It was just a "ride in the elevator" and he almost freaked out. I have valid concerns about coming across too forward yet. I know where you stand, thank you.

 

You misunderstand. I mean that if you ask him to get lunch, it's just lunch -it's no big deal. If it's that big a deal to him that he says no and runs away than either he is not available to date or not interested in dating you -either way you'll know. I don't think I'm playing devil's advocate at all. I think you're reading far too much into this situation and making a ton of assumptions about why he's not asking you out, all of which will make it much harder for you to suggest lunch and get your answer. If he almost freaks out by a ride in the elevator then most likely he is not available to date or date you. Asking him to get lunch will resolve it once and for all. Or, you can do nothing and decide it's not worth it. No biggie either way. I married a very shy guy who worked in my company but on a different floor and in a different department. We met and spoke three times at company events and 9 months after we first met he got up the courage to ask me to lunch. If he hadn't we most likely would not be together now, married and with an awesome child. That is why I'm a fan of you asking him to get lunch to see if there is any potential in the future to go on a real date.

 

I don't care how casual his office is. It's an office. It's his job and you don't work there. You're an outsider. No matter how personal they are with each other he is still an employee there -he's not going there to hang out and shoot the breeze. It's how he makes his money and that might affect whether he's willing to date someone he has to see in the building regularly even if you are at a different company.

 

Just wanted to clarify -good luck!

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