Search Results: how should i get his number

Should I reach out to him or do you feel it’s awkward and not appropriate?

Yesterday my mom was in town and we went out to a nice restaurant and our waiter was a nice guy who looks like he’s a tad younger than me but we are in our 20s.. he was very nice and he was a nice looking guy.

He was attentive and he told us some of his favorite things on the menu. He did a good job and maybe in the back of my mind I thought he was cute and maybe said it but didn’t really think anything of it.. just a guy doing his job..

He did make eye contact with me even when just talking to my mom.. He did ask questions and asked how I got here since I’m not from this state.. I told him I was an art teacher and I told him how I stopped teaching in December to pursue something else and he tells me he understands completely and he just changed his major in college… did a 180 from film media to production…

I could tell my mom was up to something.. but the conversation was nice and he said he could give us recommendations for things to do and he tried to see if there were any free art tickets to go to the art museum.

My mom embarrassed me and told him I need to meet people and hang out and she ask him for his number and she says “maybe you have friends you can hook her up with “

It’s awkward for me and I tell him that he doesn’t have to do that or feel obligated to and i apologized… it was kind of a pause maybe because it’s awkward but he does say sure and he writes his number down

But I don’t want to reach out because I don’t know if he really wanted to or felt obligated

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.