Dear Gabby,
I know that you give lots of different kinds of advice; however, your relationship advice seems to be on point the most, so I hope you can help.
Here goes nothing. To start, let’s set the scene. I attend this one church in Dayton and there’s a bunch of beautiful boys who go too. They always sit and talk with me. Usually, light flirts are exchanged. That has given me the encouragement to ask one of the guys out. Here’s my issue: he is never by himself! He’s always surrounded by his friends—how awkward!
What should I do? How can I get him one-on-one to ask him out? Or how can I casually ask him out without the awkwardness of his friends staring…?
Cordially,
An awkward boy
Dear an awkward boy,
I do give lots of advice and relationships seem to be at the top of my list. Nowadays, I think everyone wants to find that connection with someone I think we are so disconnected because of the digital era.
So, I’m sure just those “light flirts” feel nice to actually experience feelings in person. I think you should just trust yourself and go for it. What’s the worst that can happen?
I think it’s easier, honestly, to ask someone out in a group rather than one-on-one because the pressure is much lower. I think it’s more casual if you suggest hanging out in a group rather than a one-on-one date. This will give you a chance to get to know him, but without the stress of a “first date.”
Once you hang out with him in a group you can get to know his interests and start hinting towards hanging out one-on-one. Maybe use the date to sit next to him and find things that you have in common so that you can suggest another date that could be just the two of you.
I think starting off in a group is nice because it’s not as awkward and it gives you a chance to find out what things you have in common and what you may potentially like in his personality.
By the end of the night, maybe suggest that you two should catch a movie or chat more about a certain subject that you found that you had in common. This will give you a chance to finally get that one-on-one time that you’ve hoped for.
Good Luck,
Gabby