TLDR – Spent the weekend with a guy under the assumption it’s casual, but see potential for more. Am I picking up valid signs or am I just fooling myself, and how do I approach the topic to him?

A couple disclaimers – I know I fully put myself in this situation and I’m currently beating myself up for it, so please take it a little easy on me lol. I’m also pretty new to casual dating (and have realized it’s not for me) so I’m sorry in advance if my details & questions are stupid

Background – I matched with a guy (M31) on Tinder about 3 weeks ago. He was in town for a wedding and lives 1.5hrs away, but visits fairly often to surf and visit friends. He said he’s looking for casual, and I said I got out of a relationship 5ish months ago and am not jumping into something serious right now. We couldn’t make the timing work, but said maybe when he’s back. He’s taking a class for a very intensive field (school M-F, studying weekends) so he wasn’t sure yet when. We exchanged numbers and he added me on Instagram. He likes my posts and sent a couple random messages based on my stories.

Fast forward to now. He texted asking if I was free this weekend because his schedule was lighter. We originally planned to get a hotel on Saturday, but he ended up coming to my apartment on Friday too. We had sex, he spent the night, we hung out in bed cuddling all Saturday afternoon, then he asked if I wanted to get food with him. I had a yoga class later and he was planning to see his best friend, so we coordinated around that. He wanted the three of us to eat together, but I have social anxiety and got nervous so I was honest with him and he was totally fine to adjust the plans. We had a late lunch, he dropped me off at yoga, and picked me up a couple hours later. We went to the store to pick up some wine and food, then went to the hotel. After we ate and showered, we cuddled and watched tv until we fell asleep. In the morning we had sex and cuddled until it was time to go. He asked if I wanted breakfast but I wasn’t hungry yet. He dropped me off and that’s where we’re at now.

Other things that felt confusing – Wanting me to meet his best friend, holding me while we walked places because I was cold, holding my hand when we’d cross streets, kissing me in public constantly, cuddling me all night both nights, talking a lot about next time and planning when he’d come down next (he kept saying school is crazy until December but would then try to coordinate something in a couple weeks). Saying things like “this will hold me over until I see you again” (this felt sooo confusing), “next time he can stay longer, he “can tell I’m a wonderful person.”

While we hung out, he was such an open book. Talking with and getting to know each other so genuinely, it felt amazing. He hit super different and I could feel it right away. I prodded a little about where he stands with relationships. He said his last relationship ended in February, he learned a lot about himself and himself in relationships, before that he was single for a long time, and he wants to settle down eventually. That’s about all he said so I left it so as not to be weird lol

Like I said at the beginning, I’m pretty new to casual dating. I’ve done it a couple times before and it was way more transactional. But my head is swimming with how sweet and thoughtful he is, and how well we get along outside of sex. I really enjoyed spending time with him and feel like I want the potential for it to eventually develop into more, even if it’s not right now. It’s true I don’t want to jump right into anything serious, I want to take my time and make sure it’s right. But I also know I’ll overanalyze wondering if there’s something with potential here. Maybe this is just how some guys are with casual dating and I’m naive lol.

When he got back we texted a bit and I asked if after he’s done studying for the day can we talk. His response “yeah yes :))” I don’t wanna mess this up but since we’ve barely talked about what this is, I want to get a clearer understanding. How should I approach this that doesn’t come off too strong but also helps me level set with myself? :/

Thanks in advance for your perspectives

7 comments
  1. The issue about men is they don’t really think when they do a lot of things. You can’t really take anything they say, and even a lot at what they do, in a literal sense. Like you would think that if a man is aggressively trying to integrate you into his social circle he has romantic feelings for you, but really, who the hell knows?

    For my HONEST opinion, I’m sure he likes hanging out with you and enjoys your company.

    If this is already taking a toll on you, when he tries to hang out with you next, just say something along the lines of, “Hey, thanks for reaching out. I’m not really sure if I can do something casual anymore. If that doesn’t work for you then I understand, and best of luck!”

    If he likes you, he’ll do what he needs to do to keep you around. if it was casual to him, he’ll float away.

  2. yeah all the stuff he said/did is nothing out of the ordinary for guys even w it being casual. if you want it to turn into anything i wouldn’t sleep w him anymore

  3. Honestly, it sounds like you two are having a pretty natural connection.

    If he’s being straight forward with you about realizing how he is in relationships and his apprehensions about that, then the best thing you can do is just listen and understand.

    If he’s being an open book with you, and doesn’t seem to be dodging questions, then you should just be honest with how you’re viewing things with him as well.

    If he’s serious about only wanting something casual, he will make that clear.

    If he tells you that he feels a connection, but isn’t sure what he wants at the moment, do not let yourself get too involved. That can lead to your feelings getting hurt, and just confuse you way more.

    If he genuinely does want something more with you, he will make that decision, and make it clear to you as well.

    Good luck to you!

  4. What about all his other girls? You know he has a bunch. I’d wait and see if he contacts you again and how soon

  5. I think the biggest obstacle is going to be the distance issue.

    If you didn’t live so far away from each other I’d say just be direct with something along the lines of “I had a great weekend. I thought I’d be able to keep things casual, but after getting to know you I don’t think that’s something I’ll be able to do. I hope you feel the same because I really like you and would like to keep seeing you, and hopefully turn it into more over time”.

    You can still go with it, but the distance, combined with how busy he is, is just going to suck so much for both of you. Personally I’d *want* to keep it casual for now, and re-assess once he’s done school and is able to move if he wants. If that’s possible for you to do that is.

  6. “Hey, I know we were just doing casual but I like you and our vibe, and I’m open to seeing where this goes. Are you?”

    Then, you get your answer. If it’s not an enthusiastic yes, then it’s a no, and move on and learn from it.

    This isn’t rocket surgery you just have to ask for what you want.

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