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How do I ask him out on a date without it being awkward?

Tagged as: Dating, Friends<< Previous question   Next question >>
Question - (1 September 2010) 1 Answers - (Newest, 2 September 2010)
A female United States age 30-35, anonymous writes:

I asked a similar question before but it got overlooked so i am going to rephrase it and such.

I met this guy, Im a sophomore transfer and he is a junior and we've hung out a couple of times. we've always hung out in groups (of his friends) but we tended to stick with each other, not in like "we're together" sort of way, but more like "i feel comfortable around you and i know you the most".

i want to hang out again, and he has made it apparent he does too cause on sunday he was like 'see you tomorrow okay?' but i dont know how to go about it without it seeming threatening, you know? so i never saw him and its now wednesday. plus i know he is always with his cemented group of friends, probably and i just feel like it might be clingy? or something? i was raised in an environment where guys and girls arent really ever "just friends" and even though i have finally opened my mind, its still engrained in me and its a terrible trait.

i want to maybe go to a show with him or something but i dont want to go alone.. but i dont know his friends.. i could ask the girls i know if they wanted to go.. and then invite him after? hm. i might meet his friends this weekend because i think some sort of party is going on. but until the weekend, i dont want to ignore him, you know? i saw him around twice since sunday but we both didnt say anything because it was a quick pass by and we were both in conversations. i make everything with guys so awkward.

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A female reader, tennisstar88 United States +, writes (2 September 2010):

tennisstar88 agony auntFirst off sorry your question got overlooked, we agony aunts try to answer everyone...some days are more bombarded with questions than others.

Now, when I was younger we did group dates. Where you grab a friend and he brings his friend so that way everyone has a match. I would observe his friends next time when you hang out with them and see which one would be a good match for one of your single friends. In fact, you can bring some of the girls to the party to mix friends and see if any are a noticeable match. It often works, sometimes they don't get romantically involved but walk away at least friends. After the party, ask if he wants to do a group date to the show. He'll most likely say yes, you just got to work on your shyness. Don't let him get away!

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