Search Results: talking with family

In December 2024, I met a guy on an app and was instantly attracted to him. He expressed that he found me pretty, which made me feel special. Despite the age difference of 1 year and 10 months—me being older—I didn’t think it would lead anywhere serious. However, I was pleasantly surprised when we began talking every single day. He would text me at any moment, even while he was at school or at practice, sharing pictures of what he was doing. Our conversations often stretched late into the night, sometimes until 1:00 AM, and he consistently sent me good morning texts that brightened my day.

As our connection deepened over the months, I noticed that he was genuinely invested in my life, asking about my family and recommending places he thought I’d enjoy. His enthusiasm is evident in his texting style; he often double, triple, and even quadruple texts, which shows how much he enjoys communicating with me. However, about six months in, while he was on vacation, his good morning texts stopped, although he still reached out regularly.

Now, nearly a year into our relationship, I’m left wondering why he hasn’t asked me out. It feels like we have a strong bond, akin to a romantic relationship, yet there’s no official label. He has shown signs of jealousy when I mentioned dating someone else, which makes me think he has deeper feelings for me. Despite our closeness, I’m unsure if he sees me as just a close friend or if he’s hesitating to take the next step. Our dynamic is unique, filled with warmth and connection, but I can’t help but wonder what’s holding him back from making a move.

I work in financial aid remotely and currently also live with family. I had a 1:1 with my boss today since I was out of the office earlier this week, there is a tricky case we’ve been in contact about only over instant message during the week. When I decided to bring it up, I figured it’d be best to explain it again before she made a decision. I start the convo with “Let me see if I can explain it again to see if that’ll clear things up” or something along those lines. My mom overheard and asked if everything was okay, as the convo sounded serious and thought it came across as if I was possibly talking down to that person. She said my tone was respectful and that line threw her off but when I explained, I guess it gave context and she no longer thought I came across as overstepping I guess. My boss didn’t have a reaction though…