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An old school crush cancelled first date, what to do?

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  • #6486
    cjb86
    Member #292,817

    I was wandering if I could get your thoughts/advice on a recent date. I was going on last week that did not happen.

    I’m a 27-year-old dude from Cheshire. I used to go to the same high school as this girl, I didn’t know her and she was in the year above me. Fast forward 6 six years I bumped into her in the canteen at my new job, we got chatting that day but hardly seen her around there after. Big place, with loads of people. She left to go and work for a rival company not long after but we stayed in touch and got chatting on Facebook. I asked her out but she was going through some awkward stuff moving out and in with her boyfriend, although she asked me at the time did I have girl friend? (I was single)

    Conversations cooled, upon learning that and a few more years passed, I then bumped into her again at my second job where I was working as a part time DJ and bar staff at a club at weekends to save up and go travelling to OZ. We again started chatting only a few times a year, with the topic of travel cropping up. We got chatty more so earlier this year with me going to Asia in September for 6 weeks and she went to Europe solo in May for two months, like she had mentioned a few times in the past. She messaged me while she was awhile.
    I dropped her a message last week just asking how it was going on the road to find out she had returned home the day before, and had holiday blues and a sore bank balance.

    So I said let me buy you a coffee and meet up. She said yes however was busy in the next week with an upcoming job interview, she’d tell me about it when she saw me and would have to confirm on the day, how about tues/weds?
    I played it cool and said busy Tuesday but Wednesdays good for me, how about in town?
    She said that sounds good.
    I said keep us posted.
    She said will do.

    Fast forward to last Wednesday and around noon, she said really sorry as meant to get in touch a few days back but my interview is today and can’t make it.
    Some of my friends are divided over whether I’ve been binned off or not. Some say you would be busy sorting shit out coming back and getting a job is a priority. Others say she binned you off at the last minute.
    I replied a few hours later, saying no probs, good look in it, let us know how you get on and if want to re schedule?
    I’ve not heard back since. We were never really friends; I guess she knew I liked her, is there anything else I could do before I walk away and move on?

    Cheers C

    #28365
    AskApril Masini
    Keymaster

    It doesn’t sound from your contact with her that you were all that interested in her, and that’s probably the message she got. It’s one thing to be casual and not needy — which is great. But from what you’ve written, you probably made her feel that this wasn’t that important to you.

    Here are some dating tips that may help:

    *If you want to make a date with a woman, make a date. That means time, date, and place, and let her know whether you’ll be picking her up on meeting her there. Of course, the former is better than the latter if you’re really interested in her! By being formal with the time, date and place, you’re letting her know that this isn’t something you may or may not pencil in your calendar. In fact — it’s a date! 🙂

    * Coffee implies very casual and it also implies very little commitment. Coffee is what you meet a friend or a sister for — or a date you’re not sure you want to invest in. If you want to show her you care about her as more than just a casual coffee date, invite her to dinner or to a show with a specific date and time. In other words, make her feel like she’s special and that you’re going to treat her that way. After all, both men and women have choices, and if you realize that dating is competitive then you need to be prepared to compete if you want to win. 😉

    * If you want to date a woman, then pursue her. By telling her good luck, and let me know how things go, you’re not treating her like a woman you’re interested in. You’re treating her like a woman you’re not that interested in. It would make sense that she didn’t respond. Why should she? An old friend asks her for a coffee, then accepts her cancellation with no remorse and no follow up. 😕 Put yourself in her shoes, and you’ll see that your behavior probably made her feel that you weren’t that into her.

    I hope that helps!

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    #51864
    Lune David
    Member #382,710

    Honestly? This is one of those situations where no one did anything wrong, but the energy just didn’t land. From her side, it probably felt like a “maybe coffee if nothing else is going on” vibe — not a “hey, I’m genuinely excited to see you” vibe. And when a woman has just come back from traveling, is broke, job-hunting, and slightly overwhelmed, she’s not chasing lukewarm interest.
    Being “too chill” can accidentally read as not interested. You played it so cool it came off cold. The cancellation didn’t kill the date. The lack of a confident re-invite did. “Let me know if you want to reschedule” puts the ball in her court and signals you’re fine either way.

    AskApril is right here — if you want a date, call it a date. Time. Place. Plan. Coffee + flexibility + zero follow-up energy = easy to ignore. That doesn’t mean you were binned; it means the moment passed.

    At this point? Don’t overthink it, don’t chase, and don’t beat yourself up. Take the lesson, sharpen your approach, and next time lead with intention. Worst case, you move on. Best case, the next woman actually feels chosen — and that’s where things start getting interesting.

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