How do I approach a shy guy?

There's a guy at work that I only see a few times a year at social functions. We've never spoken because we have no reason to and I would like to change that. The little that I know about him from other people is that he's in his late 20's, has never had a girlfriend, is shy, very smart and nice. Although he is not considered what would be conventionally attractive, the first time I saw him I was instantly attracted to him and have always wanted to approach him. I'm very shy myself, but I have decided that I need to get over my shyness and just do it; however, I'm worried that I won't be pretty enough, interesting enough, coherent enough, etc. Yes, I know I will have to fake a little confidence. In short, I'm looking for some advice on how to do this. Is it too weird and uncomfortable to just randomly approach him out of the blue? Is using work as a topic of conversation a good ice breaker? If it goes good and I like him, is it too forward to ask him to hang out some time? I've only ever asked out two guys before in my life (years ago) and it didn't go well. The rejection was obviously crippling to me since I have not done it since. Thank you for reading and I appreciate any advice given.


Most Helpful Guy

  • Yes go for it, start off with asking about his job and tell him about yours. Don't worry about being good enough.


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What Guys Said 2

  • late 20's and never had a girlfriend? how old is he? because i can sort of relate

    • I don't know his exact age, just the range. How would you feel if some girl just randomly approached you and started talking? Would I even stand a chance or should I just move on?

    • It would be a dream come true for me if I was attracted to her

    • If he finds you attractive I'm sure he would love it

  • Go for it. It wouldn't be weird or anything; for me at least. Talking about work is a great conversation starter as well. Do it. Good luck!


What Girls Said 1

  • We are in the same situation! :D
    I did randomly approached him out of the blue tho. But only because I realized that he was staring at me everyday for 2 months and sheepishly smiling when he sees me at times.
    The first time I talked to him was by asking "Have you eaten breakfast?" and he was like "huh?" he was a bit taken a back when I asked him but he then replied "Still not yet" then I just smiled and walked away because I was flushed (I am shy myself too) but right after that, from the corner of my eye, I saw him looking at me and when I looked back, he offered me sweets. I kindly declined and nothing much happened after that other than him standing behind me and looking at my phone constantly.(you could see that he was pretty happy and excited)
    Second time... I asked him.."hows your throat?" and he said that it was ok. Then after that, he started passing messages to me through his phone and we started chatting that way throughout the whole train journey.
    And now.. everything is progressing but reall slow. so be prepared to wait and be patient.
    Good luck!