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Ask Ashley, Relationship Enthusiast
Category: Relationship
Satisfied Customers: 18
Experience:  Having built my reputation in this area of expertise, I have conducted workshops on relationships. Let's discuss your issues.
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Hi, I have a question about a really shy guy. Weve known

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I have a question about a really shy guy. We've known each other for more than a year, we see each other almost every week, socialize with the same people, but it's very hard for him to talk to me. I know from people who know him he is extremely shy and he likes me. I've approached him a few times and he is always so happy when I go up to him but I'm starting to get really tired of doing that. If I didn't know he liked me I would give up but he is a really good man and I do like him a lot. I'd like to get to know him but I'm running out of patience and ideas on how to deal with this.
My question is: do you think trying to talk to him openly is a good idea or would scare him away? When I go talk to him he gives me a hug, is very happy and chatty but he won't make the first move. After all this time I'd like to tell him that honestly I'm confused and not sure if he really wants to talk to me, and I was hoping to get to know him. I don't know him enough and I'm thinking it could go either way: he might be super happy I'm clearing the air and we can finally start talking like normal people, or he might get scared that I'm expecting something he can't give... We are grown up people in our 30s, not high school...
Thank you for any guidance you could give me.

Ask Ashley :

HiCustomer what a situation! To begin, please know that the best advice I could give is the kind I would take myself.

I encourage you to say something along the lines of, "I'm going to a movie on Friday; I'd love for you to join me. You're such a cool guy." He will most likely accept, as he likes you. Continue to establish trust and rapport with him by being the one to initiate plans if you have to. Furthermore, help him with things. This could be offering an ear when he has a problem, taking an interest in the things he likes, or doing any other kind of kind deed. If he accepts on a regular basis and it is apparent that he enjoy your company, he will open up to you in time.

By taking these steps, you two will begin with a solid friendship and possibly even more.

I hope my answer has helped you. If you feel that it has, please kindly accept my answer. Good luck.


Do you think he would react positively if I tried to talk to him openly about the situation?


I've tried all these things in about a year and he is still having a hard time


at this point I feel I need to lay the cards on the table and make things clear or move on

Ask Ashley :

Given these circumstances, yes, you must speak openly about it. It's unusual for him to have difficult with intimacy due to his shyness, but tell him your true feelings and ask him about his.

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