Search Results: he has never had a girlfriend before

For context, my brother has been dating his girlfriend, P, for two years. I absolutely adore P—she’s like the sister I never had. Long before they began dating, however, I met her brother, T. He and I are in the same grade, only about six months apart in age.

I first met T in seventh grade, when he was still a bit of a “geeky” guy. By the middle of eighth grade, I had my first boyfriend and met P for the first time around Thanksgiving. Back in seventh grade, I had a small crush on T, but it was nothing I ever considered acting on.

During freshman year, T and I had science together and started talking occasionally. I began to realize I still liked him. As our siblings grew closer, so did we. Whenever we passed each other in the hallways, we would exchange smiles—he has the cutest dimples when he smiles.

By the end of freshman year, I wanted to ask for his number, but I was too nervous. He was talking to someone at the time, and I didn’t want to overstep boundaries; if I were in that girl’s position, I wouldn’t want him giving out his number to other girls.

I hadn’t seen him for about three months until today, when we had back-to-school night. He was there with a friend, and he smiled at me like no time had passed. Later, he came over to my house because he, my brother, and P were going to the lake. When I saw him, my heart skipped several beats. I tried to keep my cool, distracting myself by making cookies and watching a show.

I don’t know if he’s dating or talking to anyone. If he’s not, I’m wondering if I should ask for his number and get to know him better. Before pursuing anything, I would make sure P was comfortable with it, because the last thing I’d want is to betray her trust or cross a boundary in our friendship.