I’m (M) currently in the very early stages of OLD conversations with two promising women, which is rare, because as I’ve posted in another thread, I’m picky and it’s hard to meet anyone I want to date, and in general, I really don’t like trying to date multiple people at once.

However, one is going to be unavailable for weeks, and is going through a rocky breakup. I’d guess our first date would take at least a month to get to, which normally wouldn’t be a big deal – I like taking a long time to get to know someone. Our communication styles match, and I think she’s super pretty… but I have to wait.

The other woman is also incredibly cool, and our conversation has been great so far. I also really enjoy her communication style. And she’s more available, it seems. She’s new to town and I could realistically fit in a few dates before the other one is available.

I guess I have some reluctance to go all-in on #2, but worry about missing out on #1. In a perfect world, I’d schedule some fast drink dates to check compatibility. Now I don’t know how to proceed.

Thoughts?

18 comments
  1. > one is going to be unavailable for weeks, and is going through a rocky breakup

    What is your goal ? If it’s anything more than casual and no strings attached then I would not go on this date. Why is #1 even an option? This makes no sense to me. She’s not available physically or emotionally. Go out with #2.

  2. Just date #2. By the time #1 is available you might have stopped dating #2 anyway, or you might be dating #2 long enough that you’re not interested. Either way your question will be answered for you.

  3. If I was interested in both women, I would date both of them according to their availability. I wouldn’t get too hung up on schedules. I currently see someone on weekends and another person a few times a year, and these are both very valuable and rewarding connections for me.

    But if you *really* don’t like to date multiple people, I would suggest you choose the prospect that has the highest chance of being able to give you the things you want out of dating. But definitely go out with the second woman at least once! You are not really in a position to go “all out” with anyone just yet.

  4. You’re thinking about holding out for the one that is going through a rocky break-up right now? Really?

  5. If it was me, (I’m a 33f so you can take this with a grain of salt) I would pass on number 1. She’s literally telling you she’s not ready to date and how would she or you know that she will be ready in a month? I get that she’s unavailable to meet until at least a month maybe for other reasons than the breakup, but still – a lot or very little can change emotionally in a month.

    If you are looking for something serious I would give #2 a full chance, rather than still hanging on to #1 potentially being able to see you.

  6. How many in person dates have you been on with each?

    Edit: It sounds like you haven’t been on a date with either. Is that correct? If that’s the case, there is no choice to be made. You are getting wayyyy too far ahead of yourself.

  7. Both could literally ghost you tomorrow. #1 could end up reconciling with their current relationship. Or decide they’re out of the dating pool for the rest of the year. You’re way overthinking this.

    Be supportive of #1, keep in touch for now and understand that a “rocky breakup” doesn’t mean they’ll magically be emotionally available, stable, and ready to date next month.

    Get to know #2, since you haven’t met either in person. They could be a great match, and you know they’re (from what you said) available and ready to actually date.

    This is a great example of the “cart before the horse” analogy, it’s not even really a question of “strongly different availabilities.” #1 isn’t available now, may not be in a month, and may not end up being so at all.

  8. You have too many eggs in these baskets. You haven’t met either one. Great text conversation can absolutely die the moment you meet in person. In-person chemistry can be like an on/off switch. And you need both people to be on.

    Just go on the dates. This is not a big deal. You haven’t even started dating either one. There’s definitely no ‘all-in’ at this point.

  9. Go on both dates, and keep swiping to try to meet someone else who you think is as pretty as the “pretty” woman.

    Keep in mind that if someone from online is talking about scheduling something weeks out, there’s a very low likelihood they will ever show up to meet you. It’s possible, but keep your expectations very low. She might just be using you for emotional support during her breakup to feel validated that she can match with other guys, and she could end up getting back together with her ex. Basically, until you meet in-person, you should assume that she is a mirage.

  10. Hard pass on number 1. Wait until someone is completely out of their previous relationship and has had time to recover before starting another. If they’re “still involved” (unless it involves kids…that’s a different story)….nope.

  11. Question from an autistic person. Is it normal to have talked about past relationships and breakups etc? How does this enter conversation?

    If it were me, I’d arrange as many dates as you can. The conversion rate will be significantly lower than 100% so you need to maximise the amount going into the funnel.

    Obviously don’t get too invested in the one going through a breakup, though. All it takes is the ex to get horny, realise his mistake and take her back.

  12. why would you want to date someone who is currently going through a rocky breakup?!

  13. You haven’t gone on a date with either of them? Have you even met #1? How do you know she isn’t using you for some emotional comfort while going through this breakup?

    Either way I wouldn’t think so much of this when (if) you haven’t even met. I understand it’s hard to multi date but you aren’t dating either of them. In person chemistry can be starkly different from online interactions.

    Basically don’t close your options. i.e. #2, or #3, #n until you’ve at least met #1. Overall I would not recommend dating someone who’s not even out of their current relationship, but that’s on you.

  14. Youre overthinking things.

    Keep lines of communication open and go with the flow.

    It takes me 4-6 in person dates to really gauge my own serious interest.

    Keep swiping and find a connection that works for you.

    Fwiw, ditch the mid break up woman. Most people need time to heal. You dont want to be a rebound

  15. The way I am reading your responses is you really are just going to hold out for #1 regardless of experience and advice here. So just do it. It’s not going to work out, but I guess you have to learn that on your own, bud.

  16. .#1 isn’t going to be available physically or emotionally. Going through a bad break up? Red flag.

    Just invest in #2.

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