I went on a second date with a girl, I think it went really well, but it was weird and was wondering if this happened to anyone else?

So I went out with a girl about a week ago, it went well but I dropped the ball on the kiss at the end. We tried to set up multiple dates after that, but for one reason or another, our schedules didn't match up.

Tonight she asked me to go out with her for Halloween to a bar. She was going out with her brother and sister-in-law as well, so it was going to be the four of us. I knew this going in. So I get there, we go through the introductions and it became obvious to the brother that I wasn't just a friend and he told me (in front of her) that he was very protective of her and that it's ok as long as I just have my arm around her.

A bit later, they went to the bathroom leaving me and the girl I was with alone, and this time I didn't drop the ball and I went in for the kiss. It went really well and we made out periodically throughout the night. But literally every time we would start to get close, the brother would come charging over (he was a knight... with a plastic sword for halloween). He was always looking, and always had an eye on us. But it started getting to the point where the girl didn't care he was there and she just said "it's ok, I have plenty of dirt on him too". We danced and made out for a good portion of the night and she seemed to really enjoy herself. Her brother insisted on walking her home so I didn't get to kiss her goodnight because he was watching us like a hawk... all things considered, I think the brother liked me, even though he did catch us kissing at one point haha.

Has this happened to any of you? Have you ever been on a date with a girl where a family member was just there watching? I'm not going to lie, I thought it would suck, but it actually kind of made the night better, because it was sort of like the forbidden fruit thing. Whenever he would leave, she was all over me, which was really exciting haha.


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  • Sounds like things went well. The brother probably just doesn't want to see the one-and-done thing with his sis, so if you are really interested in her it's looking good.