Q:

Almost 3 months ago I briefly met a beautiful woman, kind of by accident. One of those right time, right place situations. We exchanged numbers, and have been talking almost every day since. We live in different cities. She recently came to visit and it was a blast! We did hookup but had a conversation where she said that she really likes me but due to a bad break up 5 months ago she’s guarded and not looking for something serious at the moment but in the future maybe something can develop. So my question is… how do I pursue this without getting my feelings hurt? Or what is the best way to go about this situation for the both of us? I don’t want to stop talking to her but I don’t know how to navigate this. I myself have been single for 2 years after taking a break from dating after a breakup.

A:

I’m going to start with your main question: how do I pursue this without getting my feelings hurt? The very short answer is you can’t. I’m not saying you’re guaranteed to get your feelings hurt, but rather that it’s impossible to pursue this with a guarantee that you won’t get your feelings hurt. That’s just sort of the way the world of dating / love / hearts / connections / sex / feelings work. When you put yourself out there, it’s possible that in the end, you’ll be hurting. But a life without taking those risks is not one I would particularly want to live. So let’s zoom out and look at what’s happening here and talk about the risks / rewards of continuing to navigate things with this beautiful woman you met kind of by accident almost three months ago!

Honestly, this could be a pretty fun and chill thing. You’re currently long distance, you had a blast when you were in the same place, you like each other, she’s communicated that she’s not open for anything serious but could be in the future. That sounds fun! What if you both agreed that this is a fun and casual thing, and then continued living your lives and continued talking to each other and occasionally visiting each other, and just sort of see what happened next? It doesn’t have to be a big production; it could just be easy.

The one thing that makes me think that might not be the route this journey ends up taking is the fact that you say you’re talking every day, and that you’re already worried that your feelings might get hurt. It’s true, what I said in the first paragraph of my answer, that we can never entirely avoid encountering hurt feelings in our lives because that’s just the way it goes when you take a risk with your heart, but it’s also true that sometimes we have good intuition and we willfully ignore it because someone is so beautiful. So dig in — ask yourself, what is it about the scenario that is making you worried you’ll get your feelings hurt?

For me, talking to someone every day immediately escalates their presence in my life, and can let my brain trick me into something is more serious than it is. That’s a habit I’m trying to work on — either divorcing the idea that talking to someone new every day means they’re going to be a Big Deal Person to me, or actively choosing not to talk to them every day. That doesn’t mean you need to ghost or cut them out — maybe you just want to actively make a choice not to talk to this woman every day. Or maybe for you, talking to someone daily is fine, and won’t really affect how serious or not serious you expect them to be in your life. In which case, that’s great data to have about yourself both for this situationship and for any that arise in your future.

If you can pinpoint some specific behavior you’re partaking in that will inevitably wind up hurting you in the future, this is your moment to take a step back and say to yourself: hey, how do I want to approach this? Am I going all in even though this person does not live in my city and has clearly stated she does not have capacity for something serious right now? Am I accepting that this can be light and fun and casual and that no one can predict what will happen next and she might never want to be serious with me, or she might find someone in her city who she does want to be serious with, or I might find someone in my city I want to be serious with, or maybe we’re polyamorous and we just stay connected in various ways through the course of our lives, etc etc etc?

The most prescriptive advice I can give is to be super honest with yourself about what your expectations are and how you can set boundaries both with yourself and with this beautiful woman around those expectations, and then stick with them and let yourself enjoy whatever is happening! If everyone remains open, honest, curious, and kind, you will likely be able to continue to experience this connection in a positive way, no matter what it may or may not become in the future, or it will fizzle out on its own with minimal hurt and sadness. I hope whatever is going to happen happens, and I wish for you many more opportunities to take a calculated risk for the sake of love in the future! Even when it hurts, I find the risk of connection is almost always worth it. Good luck out there.

You can chime in with your advice in the comments and submit your own questions any time.

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