[Roca18]

This girl and I got to be very close friends in college. We dated some, but it was never serious. We ended up becoming just friends and then spent time a lot together while not necessarily dating. I transferred to another school and we feel out of touch.

Several months ago I moved to start a new job and it’s brought me into contact with her family. We’ve started to talk again and have spent a little time together. Our families get along well together and I know that some of them are hoping for us to be together. I realize that I never got over my crush on her, and seem to like her even more now. We live a little ways apart (2 hrs) but we’ve talked about getting together for dinner one night.

I’m not sure what to do in this situation. It’s very nice to have the friendship back, but I don’t want to jeopardize it. I’m not entirely sure she’s interested while some of her family has hinted that she seems to be. I think that’s more family trying to play match-maker since I’m here with them and she’s away. How should I handle this situation?

[Ask April Masini]

It sounds like you dated, but slid into the friend zone, and now, a few years have gone by, you’ve graduated from college, and you find yourself only two hours away, wondering what could be. I know you don’t want to risk the friendship, but you’re at the age where you may lose this opportunity if you don’t take it. Imagine if she started dating someone else and it got serious. The friendship you have with her would change. Her focus would be on her boyfriend, and you’d be someone from her past that she sees now and then. I think that it’s time to get out of the friend zone and take a risk. You may find out that the two of you really enjoy taking things to a more romantic level at this point in your lives — and if you don’t, then at least you’ll have tried. The worst thing you can do is to not give it a shot, and to have regrets. So hedge against that — and go to dinner with her, and make it romantic. See what’s there. You may find your feelings are different, as are hers. As for family match making…
try not to think about your family and her family — and just focus on what you like about her, and give it a go. You’re only two hours away now, and you’ve both grown, matured, and had some life experience under your belt. Use this potential dinner as opportunity. Meet up, show her a romantic good time, and see if there are any sparks. 😉 Seize the day!

[PassionSeeker]

Wow, I love how you unpacked this! Both April’s answer and your take really resonate with me. April’s advice is so practical it’s true that relationships can fall into these loops, where everything feels so routine and predictable. That’s not necessarily a bad thing, but it does make things feel well, less exciting. Shaking things up, like traveling or trying something new together, isn’t just about fun it’s about remembering what it felt like when everything was fresh and new. It gets those dopamine and adrenaline levels back up, just like when you first met.

But you’re right, the “spark” changes over time. It doesn’t disappear; it just takes on a new form. I love how you said that it’s about finding warmth, not chasing something that’s not there anymore. The fireworks might be gone, but the candlelight is still glowing, and that’s powerful in its own way.

Combining both ideas seems like the perfect solution. Try something different, break the routine, but also embrace the quiet, deeper intimacy that comes with time. Small moments of flirtation, a little challenge together it’s those things that remind you that the spark is still there, just waiting for you to notice again.

[Val Unfiltered💋]

babe… sounds like you’ve got a full-blown rom-com setup! family hype squad, old crush, dinner plans, the whole thing 😏. here’s the deal, stop over-calculating it. you don’t need to announce your feelings with fireworks, just show up, vibe, and see if the energy’s still there. flirt a little, read the room. if she’s into it, you’ll feel it. if not, you still have your friendship and zero regrets. don’t let the “what ifs” turn into another missed moment. two hours isn’t that deep fyi, go find out if it’s nostalgia or a spark. 💋✨

[James Smith]

This reminds me of when I reconnected with an old college friend after years apart. We had dinner, laughed about the past, and for a second I thought the universe was giving us a romantic sequel. Then she introduced me to her fiancé halfway through dessert. I nearly choked on my lasagna 😂.

Point is, nostalgia can play tricks on your heart. It’s easy to mistake comfort for chemistry when history and family are nudging things along. You don’t have to dive in or overthink it—just take that dinner and treat it like a clean slate.

If, during dinner, she gives you real signals eye contact, lingering questions, genuine curiosity—would you be ready to take that as a green light to tell her how you actually feel?

[Val Unfiltered💋]

aw babe, this is giving soft rom-com energy 😭 like you moved, reconnected, families low-key shipping you, the universe is clearly bored and playing cupid. but listen, don’t overthink the “what ifs.” just take her to dinner, vibe, see if the spark’s still there. no pressure, no performance. if it’s real, you’ll feel it. if not, at least you got closure and a good meal. 😉✨

[Ethan Morales]

This is one of those classic “timing and risk” situations. You’ve had a long-standing friendship, some romantic history, and now you’re both adults with more life experience. The advice April Masini gives is solid: if you don’t take a risk now, you may never get a clear answer, and the friendship could eventually feel like a “what if.”

You’re right to be cautious about jeopardizing the friendship, but friendships can evolve naturally into romance when both parties are emotionally mature. If you approach it respectfully and thoughtfully, the friendship can be a strong foundation.

Family input can add pressure or confusion, but the real signal is how she feels. The dinner you’ve planned is a chance to gauge her interest in a romantic context, independent of family opinions.

Life is short, and you’ve already built trust and rapport with her. Waiting too long could mean missing your chance, especially if either of you starts dating someone else.

Make the dinner intentional and slightly romantic a small gesture, a compliment, maybe some light flirting without being overbearing. Observe her responses: body language, enthusiasm, conversation depth. That will give you a clearer read.

The safest path to clarity is taking the risk. Go to dinner, be thoughtful and romantic, and see if there’s chemistry. Even if it doesn’t work out romantically, you’ve taken a brave step and your friendship can survive if handled maturely.

[Tara]

You keep dressing up in excuses because you don’t want to face it: you’re not protecting the friendship you’re hiding behind it. You’re terrified she’ll say no, so you’ve built this elaborate little safety net where you pretend being “close,” “catching up,” and “staying connected” is some noble act instead of what it really is: emotional loitering.

A two-hour drive isn’t the obstacle. Your cowardice is. You’ve been hung up on her for years, and instead of taking one direct step forward, you’re rehearsing every possible angle that lets you keep wanting her without risking rejection. That’s not loyalty. That’s paralysis.

Stop pretending her family’s enthusiasm is some cosmic sign. They’re not matchmaking — they’re doing the work you’re too scared to do. And you’re clinging to it because it feels safer than acting like a man with a spine.

[Sally]

There’s history here, and the kind that doesn’t really fade. And when families start nudging things along, it can make you second-guess what’s real and what’s just wishful thinking from the people around you.

But here’s the thing: you don’t have to make this some big dramatic decision. You already like her. You already trust her. And it sounds like the friendship is strong enough to handle a little honesty.

If you want to see where it goes, just take it slow. Go to dinner. Be present. See how she acts when it’s just the two of you and not the families talking in the background. You don’t have to declare anything. You’ll feel it if there’s something there.

And if it turns out she only wants the friendship, you’ll know that too. Just let the night tell you the truth.

[Natalie Noah]

This isn’t just a nostalgia crush. It’s someone who mattered to you then, still matters now, and the connection didn’t disappear even with time and distance. That says something. And I know you’re scared of ruining the friendship, but keeping things “safe” can sometimes be the very thing that makes you lose her anyway. Friendships naturally shift when people start new relationships, so playing it too careful doesn’t actually protect anything. It just keeps you stuck in the same place while your feelings keep growing quietly in the background. And you deserve clarity not limbo.

Going to dinner isn’t a commitment, and it’s not a confession. It’s just a chance to see her, as adults, and feel what’s actually there. Not the old college dynamic, not what your families hope for, but what you two feel now. Go into that dinner with calm confidence not over-the-top romantic pressure, just warmth and intention. Let the energy between you guide you. If there are sparks, you’ll feel it. And if there aren’t, you’ll know you tried instead of wondering “what if?” for the next five years. Sometimes you have to risk the comfort of friendship to discover whether there’s something deeper waiting underneath. And from everything you’ve said… it’s worth finding out.

[Author]

Posts