Am I overthinking this?

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Am I overthinking this?

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  • Hayley Matthews Hayley Matthews
    DatingAdvice.com
    December 12, 2019 at 2:28 pm FORUM ANNOUNCEMENT

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    Moe1021
    Moe1021
    Participant
    August 10, 2019 at 10:29 pm #205183
    Am I overthinking this?

    Hello. First time, long time.

    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.

    Thank you for the comments.

    Lost_Pup
    Lost_Pup
    Participant
    August 12, 2019 at 10:03 pm #205298

    That’s a tough one. Any other way to reach her beyond using your buddy? Maybe she comes to a game to watch ‘Player’? You could stop and say Hi, strike up a conversation and ask for her number?

    Perhaps Facebook? Since you had a nice chat and whatnot, friending her on Facebook wouldn’t be out of line…..

    Good Luck!