Falling for a shy guy...help!

Hi everyone,

I've been best friends with this one guy for almost 8 years now. He's only been in one relationship and while it was long term, it turned out to be a disaster. Afterward, he showed intense interest in someone who flat out told him that he was a pity date. It's been about three years since these relationships and he's now pretty much given up on women.

He became alot closer with me over the years, especially after my divorce last year. We recently travelled abroad and I got so many mixed signals from him. He'd always be obviously flirtatious and outgoing with me but would then immediately grow cold and distant before I got the chance to respond to his attempts. He's definitely shy around women, although I wouldn't necessarily call him love shy.

Is there something there? Does he like me? I don't want to do anything that takes him out of his comfort zone so how do I take it to the next level if there is something there?

It sounds like he may have his feelings for you come to the forefront, but then his anxiety may come after, and make him think he may not have a chance with you. I could be wrong, but i know i used to do that because of my past experiences. Made things very complicated for me and my wife.

Have you tried giving him any signals, without waiting for him to give some first?. That may make it easier for him.

Now, guys are dense (speaking from experience!) so he may not get it at first. dont be discouraged!. What may be painfully obvious to a woman is to alot of men completely oblivious.

Another route would be to straight up talk with him about it. Being direct can also make things alot easier, especially with someone with anxiety. If you guys have a talk about it, its frank, to the point, and shouldnt leave many questions in his mind. (does she like me, or am i imagining things? ect ect).

Whereas with simple flirting and signals, it can really cause him to overanalyze, especially if hes had a train wreck of relationships the last few yrs. I know lots of female friends who are flirty but have no intentions. So the direct route may be the way to go.

Just my thoughts. let us know what happens!

show him that you are interested in him, make it a bit obvious too, if he is anything like me, he can't read between the lines unless it's straight up obvious

I think the hardest thing when you're interested in someone with sa is trying to work out if he's pushing you away because he's not interested or if its because of his anxiety.

I don't have an answer to that one, I'm just empathising with you

This guy sounds a bit like me, except hes a had a long term relationship at one point, from my experience I would say you should tell him about this, women usually have no interest in me, so when that one I just mentioned started talking to me I took the opportunity

da_illest101 said:

show him that you are interested in him, make it a bit obvious too, if he is anything like me, he can't read between the lines unless it's straight up obvious

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Thats very me, I took my mom shopping when her car broke down, we stopped at the deli in the store, as we walked off she said the girl behind the counter was flirting with me.
I didnt see it at all, if she had just been straight forward I might have actually said something

Hi everyone,

Thanks alot for all your responses! I think you all are right about him liking me. Looking away when caught staring at me and getting defensive, jealously pointing out other guys checking me out--some good signs. For goodness sake, he's put out the time and money to go on long trips to Europe with me...twice! What guy just drops that much money and clears his schedule to go halfway across the world on a whim with a girl they didn't like?

I guess I'm partially at fault for why he's been so shy around me all these years. I always perceived his shyness and defense mechanisms as disinterest in me. As a result, I've always maintained a respectful distance. Also, I was always afraid of ruining an 8-year friendship by coming out with feelings that might not have been reciprocated. Hm, I'm feeling pretty stupid now. I guess I know what I have to do now--tell him. How do I do this without making him even more anxious?

vitaminD said:

I was always afraid of ruining an 8-year friendship by coming out with feelings that might not have been reciprocated. Hm, I'm feeling pretty stupid now. I guess I know what I have to do now--tell him. How do I do this without making him even more anxious?

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That is a risk, but it really sounds like he likes you, Id say just be direct and honest about it, if hes as shy as you suggest he'll appreciate it

Yes yes yes. I am EXTREMELY shy. Shyness runs in my whole family. When I like someone, I give out hints. Jumping right in and telling them I love them would be like jumping off a cliff and into oblivion. Even when in a relationship, I'm too shy to say I love them. But, I try and say it sometimes. If he's like me, then he's waiting for you to make the first step. Go get him tiger

Conspiracy said:

Yes yes yes. I am EXTREMELY shy. Shyness runs in my whole family. When I like someone, I give out hints. Jumping right in and telling them I love them would be like jumping off a cliff and into oblivion. Even when in a relationship, I'm too shy to say I love them. But, I try and say it sometimes. If he's like me, then he's waiting for you to make the first step. Go get him tiger

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Lol, rawr. You know, I'm usually pretty forward. It's just with this guy in particular that I'm turning into a shy girl. I'm really worried about rejection or what's going to happen after I tell him at the moment. Don't worry though, I'm going to tell him soon. We live pretty far away so I'll have to plan a special get-together sometime...hopefully that's a big enough hint for him of what's to come.

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Patrick Hetic said:

That's one lucky guy. I'm a pretty shy guy too so if you ever need something to fall back on.......jk I wish guys didn't have to initiate everything first though, my life would be so much easier!

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Haha...duly noted. I think part of my problem with figuring him out had to do with the whole "man initiates everything" tradition. I'm sorry you shy guys have it so bad. I'll send some good karma your way and do the initiating this time. Time to strike up the perfect balance between subtle yet direct and straight up date rape...lol...jk.