He Seems Scared to Hang Out With Me One On One?

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!


Most Helpful Guy

  • 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.

    • Ty. I am going to try to be patient, but it's frustrating. It's also kinda weird that he's worried about this because we had an "intimate" relationship. He's told me he doesn't want to be friends with benefits and has done things proving that in the past, so I know it's not because he just doesn't want to date me seriously. He is used to having his friends around us, but I'll never get to know him as well as I want with them sitting right there.

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    • Yeah, I'm not close enough to pull that one. I'll just have to see what happens. Thank you for your help!

    • Glad I could help. Good luck.

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What Guys Said 1

  • How long have you known him?

    • I've known him since last fall, but we stopped communicating around January and just now decided to see each other again. We've NEVER had a one on one date. I've always seen him around his friends and I'm sick of that! I actually told him via text last night that I wanted to hang out with him solo, and he hasn't responded yet. I'm thinking he'll probably act like I never said it and keep trying to set up these group things.

What Girls Said 1

  • If he's shy, he might be worried just because shy people tend to show their true self/act more outgoing when they have their friends around. He might be scared that he's gonna bore you or you guys are gonna have awkward silences/moments. I know because I used that method myself. I think if you just be bold with him and tell him you want to hang out one-on-one because you wanna get to know him better, you should get your point across and maybe it'll ease his mind a little.

    • Thank you for your answer. I definitely get the sense he's afraid we are going to have an awkward time. I wish he'd chill out, though, because I won't let it get awkward and if it does, who cares? Most first dates have moments of awkwardness. I actually forgot to mention in my question that I told him through text last night that I want to hang out with him solo, and he's still not responded. I'm thinking he's going to act like I never said it, lol.