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I'm a 25F grad student who's usually way too busy between my master's program and working at Starbucks to think about dating. My older brother "Dan" (34M) has a friend ("Brody," 29M) who's been around my extended family for about 10 years. We're not related by blood—our families are only connected through marriage. We were both on my little cousin's graduation trip for a long weekend. I almost didn't even go because of school, but my schedule cleared at the last minute. You see, even though I know Brody too, my brother is way closer to him. They've gone on trips together, they watch soccer games together. However, Dan didn't come on this trip so it was a lot of my cousins, and Brody and I. No Dan.
Over the five days I was there, Buddy kept sitting next to me, joking around with me, remembering random details about me from months ago that I didn't even know he'd noticed, asking about school, giving me drinks, offering me his seat, reviving inside jokes, hugging me, complimenting me, and generally making me laugh. We had one long conversation where he told me his girlfriend had cheated on him a few weeks earlier, and I may have accidentally told him I thought he was "very good looking and charismatic." He hugged me when I told him that. It clearly touched him. And then he asked me if I was seeing anyone after. And he was just there smiling.
Two weeks after I got home, requested him on Instagram... and it's still sitting there pending. It's been nearly a week and he posted in the vacation group chat (which has been dormant for weeks now) a video of him and Dan at some bar.
TL;DR: Went on a family vacation, reconnected with my older brother's longtime friend, realized my teenage crush came back in full force after five days of joking around and talking, sent him an Instagram request afterward, it's still pending, and now I'm questioning every interaction we had.
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