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?