[jay_crossroads]

I met a girl at school last fall and everything started so fast and easy that I didn’t expect to care this much. She’s six years older and has a three-year-old — at first I told myself I wouldn’t try anything romantic because of the age gap and her child. But she gave me every sign she liked me: partying with my friends, texting me, even practically asking to come with us on a weekend trip to Detroit. I froze that weekend. I didn’t make a move. Worst decision ever.
After that weekend she wasn’t the same around me. We used to hang out and party all the time; now we barely do. Still, there are moments that make me think something’s there — a movie night a few months back where I sat an inch from her and she leaned right back up close after getting up, we talked close, and it felt intimate. But I’m terrified of misreading friendly warmth for interest. She’s told me before, “so many guys think I like them when I’m really just friendly,” and I don’t want to be the idiot who ruins a friendship.
For eight months, I’ve been stuck — desperately wanting a relationship but too scared to risk losing the friendship and the little connection we still have. Every hallway at school turns into another reminder of what might have been. I’ve tried to be patient, to be a better friend, and to build up the courage, but I keep backing down when a moment could turn into something real.
So I need blunt, practical help: should I ask her out and risk losing the friendship, or keep things as they are and try to be content with whatever closeness remains? If I do decide to ask, what’s the least risky, respectful way to do it so I don’t scare her off — a direct, low-pressure invite, or a slower squeeze (more one-on-one time, small gestures)? And how do I read the difference between friendly closeness and actual interest so I don’t wreck things or regret staying quiet forever?

[Sweetie]

Hey Jay, I get it, man. That “stuck in between” feeling, more than a friend, but not quite something real, it eats at you. You don’t want to mess up what’s there, but staying silent already kind of hurts, too.

Here’s the truth: if it’s been eight months and you’re still thinking about her every day, that’s not going away by pretending it’s just friendship. You’ve already taken the respectful route by waiting and being patient. At this point, the only way to move forward is to be honest, even if it’s uncomfortable.

You don’t need some grand confession. Just say something simple and real:
“I really value our friendship, but I’d be lying if I said I haven’t thought about us as more. I don’t want to make things weird, but I needed to be honest. That gives her space to respond without pressure. If she’s not feeling the same, at least you’ll know, and you can stop living in that “what if” loop. And if she is interested, she’ll appreciate your honesty way more than another few months of guessing. You can’t control her answer, but you can control whether you stay stuck. And honestly, clarity, even if it hurts, is better than regret.

[Author]

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