The One Trick You Pull That Keeps You Single


Name: Indigo
Question: Hi there. I’m hoping you can provide insight into my situation. I met a guy on a dating site. Let’s call him “Pablo.” We went on a first date, kept it short and it was great. Later that night he text and planned another date which was 3 days later. Second date was great and before the date ended he asked when I’d be free again. I told him that I’d check my calendar and get back to him. I did and got back to him the following evening. He told me that he would get back to me. He has told me previously that his boss is retiring which greatly affects him- he has to find a new job by the end of year. So two days after not solidifying our plans, I told him that I made other plans for that day, and wished him good luck with his search. He thanked me and expressed how stressed he was and how much work he has to do AND look for a new job on top of it. I offered positive encouragement.

He did not offer to reschedule said date. And he hasn’t initiated any contact since. It has just been one day though.

I’m curious if he’s not interested or if he truly is busy. I can see that he hasn’t been active on the dating app for the past week (when we met). I’m thinking that I won’t initiate any further contact. If he wants to talk or meet up then I’ll let him take the lead. Just curious if that’s the right approach.
Age: 28


So two days after not solidifying our plans, I told him that I made other plans for that day, and wished him good luck with his search.

Wait. You mean your  rather obvious ultimatum didn’t work? That’s surprising.


No it’s not. This trick rarely works.

Listen, I get how frustrating and disappointing it is to think you’ve met a good guy only for him to cancel or fade. It sucks. But you screwed the pooch on this one. You could have just contacted him and asked, “Hey, did you still want to meet up on Friday?” Instead, you got passive aggressive thinking your threat of walking would motivate him. We all know this trick. We know when we’re trying to be coerced or have our hand forced. He read your message, knew you were playing a game, and he walked because he wasn’t invested.  I’ve done this, too, and 100% of the time it’s blown up in my face. Although, in my case, it’s when guys cancel. That hurts my feelings, even if their reason is rational. What can I say? I’m sensitive.

For the record, I think making plans and then just pretending you didn’t is rude. In this case, though, it’s unclear if he was fading or just sincerely busy.  That’s why you don’t leap to conclusions so quickly. In a situation like that, give a person a few days to a week. He told you ahead of time he was jammed up at work. He wasn’t making conversation when he told you about his work situation. He was warning you so that you would understand when he went radio silent for a few days.

He won’t contact you. Not only did you blow him off, but you were kind snotty about it. If you want to see this guy again, you’re going to have to ovary up and ask him out. Which sucks because now you won’t know if he’s going because he’s genuinely interested or because he thinks, “Why not? Maybe I’ll get laid.”

It absolutely sucks to sit around and wait for someone you like to follow up. I totally empathize, but these early stages are all about stops and starts.  People are busy and many are juggling options, thanks to all the ways they have to get dates. You have to get used to that and plan accordingly. Bite the bullet and wait it out. If they go a week without following up, you have your answer.



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8 Responses to “The One Trick You Pull That Keeps You Single”

  1. fuzzilla Says:

    Maybe he read “good luck with your search” as “good luck in your search for love” when you meant job? Because I did. I was like – huh? Of course he didn’t get back to you if you basically politely told him not to do so.

    This is why women should always keep their options open until given a clear reason not to (I suppose men should, too, but I don’t think they need to be told) – so you have more of an idea of what’s out there, and so you don’t get impatient and blow it with someone who could otherwise be a good match.

    • Eliza Says:

      Fuzz–that’s exactly how I read it…that she was wishing him luck – on finding love. Completely forgot about the job situation with his boss. This is why- emailing and texting is NOT always the best way to communicate. Things can be interpreted wrong…and then someone that doesn’t know you well enough and not vested…will just walk away, and not bother.

  2. Dave Says:

    The way I read the response, she was not interested in the guy and was blowing him off. He won’t be getting back to her.

  3. AnnieNonymous Says:

    What’s with the half-assed mind games? Dude has only 6 weeks to find a new job. If you wanted to see him, you should have just said so.

    I think you screwed it up when you pulled the, “hmmm, I’ll check my calendar and see if I can pencil you into my busy, busy life.” I really doubt you didn’t already know if you were free that weekend. He pegged you as high-maintenance.

    • mamajuju Says:

      Or perhaps OP heard that he will soon be jobless and decided to avoid him. You’d be surprised how people avoid you when you’re going through a hard time.

  4. Laura Says:

    Yeah, this is so typical in today’s dating world. People don’t want to be seen as needy and desperate, so they come across as aloof and disinterested – until they end up looking exactly like what they were trying to avoid in the first place with such passive aggressive ultimatums. And in the end, everyone is left frustrated.
    I’ve certainly been guilty of that myself. It’s pointless. I learned the hard way that the best way to make it easier for yourself is to just go out there and communicate your interest clearly – that is, none of that “Oh, I’m really just super busy, but maybe I’ll find a way to fit you into my jam-packed schedule some time next week” BS. Make it clear that you want to see them and then leave it up to them. If they’re interested, they’ll get back. If they’re not, they won’t, and there’s all there is to it. Waiting around for someone to respond sucks big time, I know, but there’s really not much else you can do.

  5. KK Says:

    Did you mean vood luck on your job search? Because i read it as good luck on finding someone. And i dont think this is fixable because if you get back to him he will think you dismissed him and are now up to something. Why dodnt you ask him if he still wanted tp meet up?
    If he wasnt interested he wouldnt reply

  6. Yvonne Says:

    “So two days after not solidifying our plans, I told him that I made other plans for that day, and wished him good luck with his search. ”

    Why did you contact him to announce this? You’d have been better off waiting to see if/when he contacted you. If he didn’t get back to you, you’d already know where you stand. It’s possible that he’s too busy to date right now, although “busy” is sometimes code for disinterested. Then again, it’s only been one day.

    If you really like him, wait a week or two, and check in with him again. However, I tend to think if a man is truly interested and available, he will ask again.

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