▲ 2 r/datingadviceformen+1 crossposts

How do I get closer to a shy guy without making him feel pressured or seeming like I’m chasing him?

I’m a female college sophomore, and I’ve developed a crush on a guy in one of my classes. We’re both somewhat socially anxious and reserved, so starting conversations has been difficult.

We first interacted when he asked me to send him an assignment. A little later, we were partnered for an exercise and bonded over both having social anxiety. That conversation felt surprisingly natural because he kept adding to it and telling me about himself. Since then, we’ve had several smaller interactions. We’ve sat together during class trips, although we usually end up scrolling on our phones instead of talking. We’ve also made small talk, exchanged looks when something funny happened, and developed a little playful banter. He has occasionally initiated by asking me questions about class, but most of our conversations have happened because the situation put us together.

He has told me that he isn’t very social and genuinely enjoys being alone. Once, I asked whether he minded me sitting beside him, and he said he would have told me if he didn’t want me there. On another trip, he chose to sit alone and explained that he simply prefers it sometimes, which I understand because I’m similar.

I recently found out that he had a girlfriend during our earlier interactions, but they broke up a few weeks ago. He never mentioned her, but we also weren’t close enough that I would necessarily expect him to. Because the breakup is recent, I don’t want to rush him or treat his being single as an opportunity I need to jump on immediately.

I’ve also become good friends with one of his close friends and the rest of their friend group. The mutual friend knows I like him. He doesn’t want to speak to the guy for me, which I completely understand, but he has offered advice and said he’ll help make conversation easier when we’re all together. He recently brought me along when he visited the guy’s dorm, but I was nervous and barely spoke.

The next day, I tried asking my crush about his major after class. He answered but immediately walked away. It was the end of class, so he may have simply needed to leave, but it made me worry that he was trying to escape the conversation. He also hasn’t added me back on social media, although he told me when we first met that he rarely adds people back.

I can’t tell whether he is shy, emotionally unavailable after his breakup, uninterested in me, or simply unaware that I’m trying to get to know him. I don’t want our mutual friend to play messenger, and I don’t want to manufacture encounters or become the girl who constantly follows him around. At the same time, I’m worried that if I completely stop initiating, nothing will ever happen because we’re both socially anxious.

Should I give him space and see whether he ever initiates, continue making occasional conversation in class, or eventually ask him directly if he wants to get coffee or food? How can I show interest without making him feel pressured—especially so soon after his breakup? What signs would tell me that he’s shy versus simply not interested?

TL;DR: I like a shy, recently single classmate who is friendly and playful when we naturally interact but rarely initiates or extends conversations. We share a close mutual friend, but I don’t want to use him as a messenger. How should I get to know my crush without chasing or pressuring him?

reddit.com
u/HoldInternational858 — 12 days ago

AITA for telling my temporary boss I had to leave work early for a doctor’s appointment after she changed my schedule at the last minute?

I (19F) have been working full-time (30+ hours/week) at a daycare for about two months as a summer job before I go back to college.

My boss is currently on vacation, so one of the senior employees, “Tammy” (50s?F), is temporarily in charge. She normally handles the schedules anyway, but ever since she’s taken over, it feels like she’s been watching everything I do. I’m the newest employee, so I understand keeping an eye on me, but it seems like she critiques me over little things while letting everyone else do the same things without saying anything.

Since I started, I’ve always worked 9:00 AM-4:00 PM.

Yesterday she sent out this week’s schedule, and for the first time I was scheduled 11:00 AM-5:30 PM.

The problem is that I had a doctor’s appointment at 4:45 PM that I’d scheduled before I even got this job. I need to keep the appointment because it’s required to refill one of my medications. Since I’d always worked until 4:00, I honestly never thought it would conflict with work.

As soon as I saw the schedule, I messaged Tammy and let her know I’d have to leave around 4:30 to make my appointment.

A little later she came outside to talk to me and was clearly annoyed. She explained that another employee couldn’t work Mondays anymore, so she needed me to stay later to help close.

I told her I completely understood.

Then she said I should have told her about my doctor’s appointment ahead of time.

I apologized and explained that I honestly didn’t think to mention it because I’d worked the same 9-4 schedule for the last two months. Since the appointment was made before I worked there, I assumed I’d be off by 4:00 like always.

She told me I needed to let them know about any appointments, regardless of what time they were, because schedules can change.

I apologized again and told her this was my only appointment and it wouldn’t happen again.

She eventually agreed to let me leave early but told me I’d have to let another coworker know I’d be leaving before the end of my shift.

I understand her point, and now I know to mention future appointments even if I don’t think they’ll conflict. But I also feel like I couldn’t have predicted my schedule changing after two months of working the exact same hours, and I told her immediately after I found out.

AITA?

reddit.com
u/HoldInternational858 — 3 months ago

AITA for refusing to support my 19-year-old best friend trying to get pregnant by a 30-year-old man she met a month ago?

I (19F) have been best friends with “Brittney” (19F) since first grade. She’s always been in and out of relationships, but one thing she’s ALWAYS said is that she hates clingy partners and never wants a relationship where she’s attached at the hip to someone.

In 2024 she started dating “Steve” (19M, almost 20). They met online, and I was already hesitant because he told her he got kicked out of his house for smoking weed. We were still in high school at the time. About 6 months into dating, he moved into Brittney and her mom’s house.

The relationship became exhausting. Steve had zero friends and refused to let Brittney go anywhere alone. Every time we hung out, he tagged along because he apparently didn’t trust her friends, including me. Brittney and I even stopped talking for about 2 months because I got tired of him always being there.

About a month ago Brittney randomly called me saying she was single. Apparently a guy from work (“Adam”) asked for her number not knowing she had a boyfriend, and she gave it to him. Steve found out, screamed at her, called her a cnt and a whre, and she kicked him out.

Honestly, I thought the breakup was for the best.

But almost immediately after, Brittney started dating Adam. After their first date she called me giggling because they made out in his car after the movies. Normally I wouldn’t care, except Brittney has NEVER acted like this before. It took her a YEAR to get intimate with Steve because she’s usually super cautious physically.

Then she dropped the bombshell: Adam is 30.

She’s 19. He’s 30.

A couple weeks later she admitted they’d been sleeping together regularly since their second date and avoiding protection because she knew I’d “lecture her.” And yes, I did. I told her she needed birth control or SOME kind of protection because getting pregnant at 19 by a man she barely knows is a terrible idea.

A few days ago she called me hysterically crying. I thought she was pregnant.

Nope. She was upset because she WASN’T pregnant.

Apparently she’d convinced herself she wanted a baby with him after knowing him for barely a month. I told her I didn’t understand why she’d WANT to be pregnant at 19, especially when she wants to become a hairstylist and open her own salon someday. Having a baby this young — especially with a 30-year-old she barely knows — could completely derail her future.

She got angry and told me I should support her happiness instead of being negative. Now she’s barely speaking to me because I “don’t support her relationship.”

I love her like a sister, but I genuinely think she’s making one of the biggest mistakes of her life.

AITA?

reddit.com
u/HoldInternational858 — 5 months ago