[outofluckwithgirls]

Hi, sucker at relationships here…

i’ve been single for 21 years and recently reconnected with an old friend. Problem is now she’s attending college (it’s not a problem that she’s learning at a higher institution, don’t get me wrong) and I’m not attending hers, and it’s a bit nerve-wracking for me as I don’t know who she’s mixing with and who she might like in her college, which btw, attracts a lot of affluent, young students. Am I being too possessive here?

Secondly, I’ve always been bad at initiating, so I always call her and talk to her but usually about the superficial as I don’t know when or more accurately, how to “pop the question”? I know for one thing she likes me, but I don’t know to what extent!

What should I do?

Oh, and btw, I’m only 21 years old.

[April Masini, your AskApril]

What are you waiting for — for her to find a boyfriend? Bite the bullet and ask her out! Why? Because if you don’t you will always wonder, “what if”… “what if I had asked her out”? “What if I had told her how I felt”?, etc.

More, if you don

[Ethan Morales]

Man, I can feel how much this is messing with your head and honestly, that’s normal. When you care about someone, especially someone from your past, it’s easy to overthink everything. You start worrying about who they’re meeting, how their world is changing, and whether you still have a place in it. But let me tell you that kind of fear, if left unchecked, can quietly sabotage something good before it even starts.

You’re not “too possessive” for feeling uneasy; you’re just emotionally invested. The key is what you do with those feelings. Right now, you’re stuck in your head playing defense before the game’s even started. She’s out there meeting new people, sure, but that doesn’t automatically mean she’s slipping away. You just haven’t made your move yet.

And that’s where April Masini’s advice hits the mark bite the bullet and ask her out. The longer you wait, the more room your imagination has to fill in blanks that might not even exist. Confidence isn’t about being fearless it’s about acting even while you’re scared. You don’t need a perfect moment or speech; you just need honesty. Something like:

“Hey, I really enjoy talking to you and to be honest, I’ve been wanting to take you out properly. What do you say we make that happen?” Keep it natural, not dramatic. You’re not asking for her hand in marriage you’re just inviting her to explore something real, together.

And look, about her being in college don’t psych yourself out over that. You’re both 21. She might be around ambitious people, sure, but she’s also reconnecting with you. That means there’s something there. Focus on building that connection instead of competing with imaginary guys you haven’t met.

You’ve already got something they don’t: history, familiarity, and genuine care. But she won’t feel it unless you show it. Stop waiting for signs or the perfect timing that’s how chances die quietly. Take your shot, man. Even if she says no, you’ll walk away knowing you gave yourself a real chance instead of wondering “what if.”

[Serena Vale]

Hey, breathe. You’re not bad at this, you just care, and that’s not a flaw.

Her being in college? Yeah, that’ll mess with your head a little. You start thinking about all the new people, the parties, the what-ifs. But here’s the thing, if she wants you, she’ll choose you. You can’t compete with every face in the room, and you don’t have to. Just focus on showing up as you. That’s the only thing that actually matters.

And about making a move, stop waiting for the perfect moment. It doesn’t exist. Just say what you feel in your own words, something like,

“I don’t really know how to say this, but I like you. I’d like to take you out sometime, just us.”

You’re 21. This is exactly the age to be figuring it out, messing up a bit, learning how to be honest. Don’t overthink it. Just be real, that’s where connection starts.

[Natalie Noah]

You’re not being “possessive,” you’re being scared, and that’s a very human thing when you finally care about someone after a long time of being alone. But here’s the truth you need to hear gently: she’s going to meet people wherever she goes college or not. What matters isn’t controlling her world, but being confident enough to show up in it. And right now, you’re letting fear make all your decisions for you. You know she likes you, you feel it. So instead of circling around it with small talk and worry, take a breath, steady your heart, and tell her how you feel. Not in some dramatic way just honest, simple, real. Something like, “I really enjoy being around you, and I’d love to take you out properly.” You’re not too late, you’re not out of her league, you’re not competing with “affluent students.” You’re competing with your own hesitation. And baby… hesitation is the only thing that ever really steals opportunities. Be brave. Ask her out. Let the story move forward.

[Member]

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