TL;DR, I am in a situation to decide whether to fly or not to meet a guy for our 4th date for the sake of the momentum. It’s not too far or expensive but I am not sure if this is going to be worth it given how early we are and the uncertainty I feel from the guy, understandably, because he does not wanna come across pushy. What’d be the wise course of action in this situation? (slept together on the 2nd date if it matters)

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His schedule happened to be erratic this month, so to continue what we have/had, or even to see we have something special, he asked me if I’d like to check out where he is now for our next date. He needs to spend some time there till the end of the year, so it’d be nice for us if I like it there. It’s one of those popular places in winter that most people would be happy to be anyway, so why not checking out.

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Due to his schedule this month, he suggested me coming to his city over the upcoming weekend, then he will spend a week in my city (where we met) week after that, then we can both fly back and forth to spend more time together between two cities. At first I asked him if he were me he would fly to just spend the weekend here with me to see if we stand good chances, and he said he would, if that’s the only option available. But since I haven’t been to where he is now and given that he’ll be there this winter and it is nice there in winter it seemed more reasonable that I visit him first and go from there. Listening to him saying he’d visit if that’s the only option definitely made me feel better as well.

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We talked about how we enjoyed spending time together albeit only 2-3 dates, and we wanted to explore it further. But the reason we ended up in this situation is because this all happened very last minute, I did not know about any of these while we were having normal dates here. He did not see where we were going, he did not even know his plan at the point. And right before he had to leave he was pretty distant due to work, which left me confused. All these added up, I’m in some deep hole where I am not sure if he even wants me or a relationship at all, but given that we just met it’s understandable that he is not sure, hell even I am not sure. It’s something I wanna explore but I am not sure, either.

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So I wanted some assurance from him, although I understand that he can’t give me much as we just met and he doesn’t wanna come across pushy, which again I can understand… I expressed my feeling about this and he said that he does not want me to do it if it makes me uncomfortable, so why don’t we can just skip the weekend trip and meet when he can come here for a week, and go from there. It’s two weeks away, feelings are volatile, we’ve met only three times, I am not sure if there will be anything left at that point. But to go on the trip for something with so little foundation, I am not feeling great about it. The fact that I’m going there to see him doesn’t make me excited exactly because of the uncertainties, because I am risking wasting my time, energy, and money. But I need to embrace SOME risk for a relationship. Then again I want SOME assurance from him as well while I understand he can’t be pushy about it — it will definitely push me away, and I know if he pushed me for it hard I would’ve felt iffy about it. And this continues in a cycle… How can I get out of this abyss?

8 comments
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  2. To be honest, it sounds like you have a gut feeling that this won’t last and/or that you’ll be wasting time and money that he may not reciprocate. I’d listen to that gut instinct; it’s never been wrong for me, no matter how unwelcome.

  3. You’ve only been on 4 dates and had sex like twice and it already sucks. Unless your ideal relationship was long distance to begin with I don’t see what you’re really getting out of this.

  4. It sounds like you have anxious attachment. It’s too early in the relationship to have these insecurities. You barely know this person. If you want to explore the relationship more, go on the trip. If not, don’t go. I don’t think he would invite you if he didn’t want you there.

  5. Okay. Not to be a cynic, but I’ve been there before. Several times. Men who travel like that have women in every city. Him saying if it’s not this weekend translates as slow down, no big deal. Three meetings is all lust and genitals, which is awesome, just be realistic. Enjoy.

  6. If you don’t think your feelings are going to last two weeks without seeing each other then it does not sound like this is worth the flight to try and bridge that gap. At least on your side.

  7. If you go and it doesn’t work out then you both know you tried, and got to go to a cool winter vacay spot. Go into it with the intention of having fun and seeing something new.
    I tend to regret the things I didn’t do more than the things I did though. So….

  8. Honestly I had a hard following all that.

    But its simple: he asked you to come which means he wants to see you. Its just a quick weekend, get your a separate room so you can have a little alone time if the weekend gets a little overwhelming. You liked him enough to go on a few dates and sleep with him so if you like him and want to keep seeing him; go see him.

    I don’t really see the problem with waiting to see him in 2 weeks when he comes back into town but if you feel that two weeks will hurt the potential relationship, then go.

    Reassurance from him of what? He asked you to come, you might be over thinking all this. Let the dating turn into a relationship if that’s what you want. Because of the distance even if its temporary, you have to put in a little effort to build the relationship. And if this weekend is a bust, then it is. There are no guarantees in life.
    If you have a specific concern, then speak to him very honestly about your concerns and see how that plays out, don’t expect him to guess what is bothering you.

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