There's this guy who is interested and who I want to get to know more, but he seems scared to hang out with me or go on a solo date. He always wants to make it a group thing with friends. I've definitely picked up on him feeling intimidated to be one on one with me. Is there anything I can do to subtly let me know he doesn't need to be worried? I'm amazed he's still like this because he's almost 30!
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When he is with a group of friends, he has a more familiar and comfortable surrounding with him. He probably thinks that if he screws up, it won't be as bad as it would if you were one on one. The next time you are out with him and a group of friends, try pulling him aside, just the two of you. If he ventures off by himself, go with him. Try this a couple of times and then try to get him out with just you.
Some men take a long time to develop a comfort around women. My pastor just retired last week. He's 66 and, celibacy aside, he still doesn't feel comfortable around women, even women on the parish staff, and he's a big, intimidating guy too. Some men are just late bloomers. I didn't work up the courage to ask a girl out until I was 20 and in college. In that case, you have to let him get comfortable around you. Show interest in him. Ask him about where he's from, the things he likes, his job, etc. Above all, though, be patient.0
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