"April Masini answers questions no one else can and tells you the truth that no one else will."

Asking an old friend to date from a long distance

Viewing 9 posts - 1 through 9 (of 9 total)
[hfe_template id="51444"]
  • Member
    Posts
  • #8179
    tmarp
    Member #374,643

    I have know her for 6.5 years. I have had a crush on her for the majority of the time we’ve known each other, and I have gotten the same vibes from her in the past. I’m cautious, and don’t want to ruin a good friendship. We met in college and have been best friends ever since. We saw each other on a daily basis. She graduated about 3 years after we met and moved to another state. After she moved, we talked infrequently. I graduated and got a job about 6 hours from her. My group of friends from college try to get together annually and catch up. We recently got together for one of our meetings, and I realized how much I like her. Shortly after, I was told by a friend (who is also a friend of my crush) that she was waiting for me to make a move.

    So I’ve resolved to ask her out, and have already planned on visiting her in about a month. The complexity of my situation is that we haven’t been communicating on a regular basis for a long time and we can’t easily get together. It doesn’t help that I found out that she’s waiting for me from someone else; it could be rumor! I have considered just calling her up and telling her how I feel before I go visit her, but have reservations about that because of the lack of recent communication. I also think this option is shallow, I’d rather ask in person rather than over the phone. I have also considered sharing how I feel while I’m visiting her, but I don’t want to catch her off guard. Since we are both introverted, she’d appreciated a heads up before I bring this up. I’m just not quite sure how to go about asking her out now.

    #35511
    AskApril Masini
    Keymaster

    You’re making a lot of excuses instead of taking action. 😉 All you have to do is ask her out, and you shouldn’t wait any more. You’ve had a crush on her for over six years – it would be a shame to let any more time go by and possibly lose your opportunity. Carpe diem!

    I know you want to ask her out in person, but since you don’t live close by, pick up the phone. Women love to hear a man’s voice, and it’s one of the things that actually bonds them to you. You may not realize this, but your voice is an attractor when it comes to women, so call her up and ask her out. Make a plan to see her and follow through.

    This isn’t complex — you’re just overthinking it. Don’t worry so much about catching her off guard — in fact, it could be very romantic if you do! And don’t worry about the lack of communication recently — because if she says yes to your date, you’ll be in touch with her a lot more!

    Lastly, don’t share your feelings — share an experience together. Have a romantic dinner or a special date where you take her somewhere beautiful to have an adventure together. If you want to build a romance together, then start by calling her, asking her out and making a plan that you follow through on. You’ll be so much happier when you start taking action — and so will she! 😎

    #46136
    Ethan Morales
    Member #382,560

    You’ve known her for over six years, had a crush all that time, and now you finally see the chance to make a move. Honestly, you’re overthinking it. The distance and lack of recent communication don’t have to be barriers they’re just excuses your mind is inventing to avoid risk.

    Take action, don’t over-plan You want to ask her out, and you want it to be meaningful. Waiting until you see her in person is ideal, but the reality is that long distance requires some flexibility. Pick up the phone and ask her out now. A call shows confidence, lets her process your intentions, and starts the momentum.

    Focus on shared experience, not confessions Instead of spilling your feelings verbatim, frame it around an experience: “I’d love to take you out for dinner next time I’m in town” or “Let’s spend a weekend together and catch up properly.” It’s romantic, low-pressure, and actionable.

    She’s probably receptive You mentioned a friend told you she’s been waiting for you to make a move. Even if it’s just a rumor, the fact that you have that sense tells you she’s likely open. If she says yes, you now have the opportunity to rebuild consistent communication.

    Don’t worry about catching her off guard Introverts often appreciate honesty more than being surprised by a bold gesture. But the truth is, being bold can also be charming and romantic. Call her, set up a date, and then show up with your genuine self.

    Long-distance isn’t a deal-breaker Many people get stuck thinking distance equals impossibility. It doesn’t — it just means you need to start the conversation sooner rather than later and show commitment through planning and follow-through.

    Stop overthinking, pick up the phone, and ask her out. Make it about the shared experience, not a dramatic confession. Confidence, clarity, and action will make the biggest impression. If you want, I can draft a short, natural script for calling her that sets up the date without feeling forced or awkward. Do you want me to do that?

    #47367
    Marcus king
    Member #382,698

    This is one of those situations where the timing and the tone matter much more than the exact words. You and her already have real history, comfort, and familiarity and that’s actually the advantage here. The thing that has created the distance isn’t a lack of feelings, it’s just life moving in different directions for a while. So the goal isn’t to suddenly “confess love” out of nowhere. The goal is to re-establish connection before you try to move it forward.

    You don’t need to message her like you’re already asking her out. What you need first is to warm the communication back up in a natural, relaxed way. Think of it as reminding each other of the comfort and chemistry you used to share. Start with small, easy, light contact not emotional, not heavy, just familiar. Something like:
    “Hey, I was just thinking about the group hang you still crack me up. How’s your week going?”
    This isn’t pressure. It just opens the door.

    #48694
    Tara
    Member #382,680

    You’re not being “cautious,” you’re being scared. Six and a half years of silence, hesitation, and overthinking doesn’t make you careful — it makes you passive. And now you’re trying to engineer the “perfect” moment so you don’t have to face the risk of rejection. That’s not strategy, that’s fear wearing a suit.

    You’re also clinging to a rumor like it’s divine confirmation because it gives you an excuse to delay and fantasize instead of acting. If she actually wanted you to make a move, she’s spent years watching you not make one. That alone should tell you she’s either incredibly patient or not as invested as you hope.

    Here’s your reality: your lack of regular communication already killed the illusion of some slow-burn romance. You don’t “catch her off guard” by telling her you like her — you catch her off guard by waiting half a decade and pretending the timing is delicate.

    Your move is painfully simple: call her before the trip, not with a Shakespeare speech, not with a dissertation, just direct honesty. Tell her you’d like to take her out properly when you visit. That’s it. No drama, no buildup, no overplanning.

    If she’s interested, she’ll make it obvious.
    If she’s not, you stop wasting emotional energy on a fantasy you’ve been nursing since college.
    Either way, the era of overthinking is done. Act, or let it go — but stop hiding behind “introversion” like it’s a shield.

    #48695
    Tara
    Member #382,680

    You’re not being “cautious,” you’re being scared. Six and a half years of silence, hesitation, and overthinking doesn’t make you careful — it makes you passive. And now you’re trying to engineer the “perfect” moment so you don’t have to face the risk of rejection. That’s not strategy, that’s fear wearing a suit.

    You’re also clinging to a rumor like it’s divine confirmation because it gives you an excuse to delay and fantasize instead of acting. If she actually wanted you to make a move, she’s spent years watching you not make one. That alone should tell you she’s either incredibly patient or not as invested as you hope.

    Here’s your reality: your lack of regular communication already killed the illusion of some slow-burn romance. You don’t “catch her off guard” by telling her you like her — you catch her off guard by waiting half a decade and pretending the timing is delicate.

    Your move is painfully simple: call her before the trip, not with a Shakespeare speech, not with a dissertation, just direct honesty. Tell her you’d like to take her out properly when you visit. That’s it. No drama, no buildup, no overplanning.

    If she’s interested, she’ll make it obvious.
    If she’s not, you stop wasting emotional energy on a fantasy you’ve been nursing since college.
    Either way, the era of overthinking is done. Act, or let it go — but stop hiding behind “introversion” like it’s a shield.

    #48940
    Sally
    Member #382,674

    When you have liked someone this long, the idea of messing it up feels huge. But honestly, nothing you have said sounds risky, it just sounds like two quiet people who never quite said what they were feeling.

    And finding out through a friend might feel shaky, but it did not come out of nowhere. You have had chemistry for years. That does not just vanish.

    You do not need some big plan. Just ease back into talking with her, a simple “hey, been thinking about you lately” kind of thing. Let it feel normal again. And when you go visit, give her a little heads up like “there is something I want to talk about when I see you.” Nothing dramatic, just honest.

    If she has been waiting for you, she will not be surprised. She will be relieved. And if not, you still tried with kindness, not pressure.

    #49331
    Natalie Noah
    Member #382,516

    I can see that your hesitation is coming from a place of care. you value your long-standing friendship and don’t want to risk it but honestly, the longer you wait, the more anxiety and doubt can build for both of you. You’ve known her for over six years and the feelings are real, so holding back doesn’t protect the friendship, it just delays clarity. A phone call is not a shallow move; it’s a bridge. Hearing your voice conveys warmth, sincerity, and confidence in a way a text or rumor can’t. You can give her a heads-up about wanting to see her without laying everything on the line just enough to prepare her, which introverts often appreciate.

    The key here is action, not perfection. Focus on creating an experience together rather than making it a confessional. Ask her out, plan a simple but meaningful outing, and let the chemistry and your history guide the connection. The romance will grow from shared moments and quality time, not from a long speech over the phone or a dramatic declaration. By stepping forward, you give her and yourself the chance to see if this crush can evolve into something real, without the weight of rumors, assumptions, or missed opportunities hanging over you.

    #49598
    Serena Vale
    Member #382,699

    It sounds like you’ve been holding this inside for a long time, and honestly… that’s probably the part that’s making everything feel heavier than it needs to be.

    You two have history. Real history, years of friendship, slow-burn feelings, and that quiet comfort that doesn’t happen by accident. And when someone tells you she’s been waiting for you to make a move? That usually doesn’t come out of thin air. People don’t “rumor” that kind of thing unless they’ve sensed something.

    If I were you, I wouldn’t call her out of the blue and drop the whole confession over the phone. That feels rushed after years of barely talking. But I also wouldn’t show up, hang out like everything is normal, and suddenly spring it on her. For two introverts, that’s a recipe for both of you shutting down.

    What I would do is something soft, simple, and honest, something that gives her space to breathe and you space to be yourself.

    Before your trip, send her a text that just opens the door a little. Something like:

    “Hey, I’m really looking forward to seeing you next month. There’s something I’ve been wanting to talk to you about, nothing heavy or scary, just something honest. I’ll tell you in person, I just didn’t want it to catch you off guard.”

    That’s it. No big confession. No pressure. Just a heads-up. It lets her prepare emotionally, and it keeps the moment grounded when you finally see her.

    And when you are with her, don’t make it dramatic. Don’t turn it into a movie scene. Just be yourself, the version of you she originally connected with.

    Something like:

    “I’ve liked you for a long time… probably longer than I ever admitted. And I wasn’t sure if saying it would risk what we already have, but I also don’t want to pretend I don’t feel it anymore. I’d like to take you on an actual date, if you’d want that too.”

    Simple. Clean. Calm.

    If she feels the same, which honestly it sounds like she might, she’ll meet you halfway. And if she doesn’t, it won’t destroy the friendship because you approached it gently, not desperately.

    You don’t need a perfect plan. You just need to stop carrying this alone.

    And trust this: if she’s been waiting for you, she’ll be relieved you finally said something.

Viewing 9 posts - 1 through 9 (of 9 total)
  • You must be logged in to reply to this topic.

Comments are closed.