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My Buddy is a softball coach. He is very good friends with the family of one of his Players. We all went to the beach recently and I met Player’s older sister for the first time. At one point Buddy, Player, Sister and myself went surfing. I paddled away from the group to set in a different spot, not unusual. Sister followed me instead of staying with Buddy and Player. We talked a little, laughed a little, but I was busy with the ocean, a passion for me, and I’m socially awkward so I didn’t get to know her like I should have. We all part ways at the end of the day and I start to think about her as I’m driving home.
Do i ask Buddy to set up another hangout so I can correct my mistakes or do I wait for it to hopefully happen on its own? Also, i don’t know how he’ll react if I tell him. He’s very protective of these girls and he might be uneasy about it. Also she’s 23 and I’m 33. It doesn’t matter to me but it’s worth mentioning.
Wait... no he's not over thinking this or no, don't do it?
Personally when I see this question in the title my first thought is always "if you are asking then the answer is yes, you are over thinking... I don't care what the question is." I also think that trying to arrange another meeting is a bad idea. You learned something during this meeting and the NEXT time you are in this situation where you feel socially awkward, you can be better prepared. That is if you DO learn from this meeting and are prepared to change the way you act.
Damn. You're not asking her to have your babies. You're asking her if she wants to grab dinner or something. In that sense, you're completely, utterly overthinking things.
Please don't be some childish nebbish and ask your buddy to do the work for you. That would be a complete turnoff. This is not middle school and you're not passing her a note in history class. Just call her. And ask your buddy if it would be okay. That would be a wise move.
Why do some people automatically think that someone they meet casually who happens to engage in friendly conversation or happens to enjoy a mutual activity is a target...or will be sitting around waiting for their call? After one meeting? She could simply be a pleasant friendly person, not interested. If your buddy invites you to other events she might also attend, just accept the invitation! What's hard about that? Don't have to force the issue. Maybe something will develop on its own. Maybe not.
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