My Awkward Dating Experiences Part 2


A week or so ago, I published My Awkward Dating Experiences Part 1, so I decided to finally write that follow up post. There’s one experience I really wanted to go into, and while I’ve had other weird and awkward experiences, I’ll save them for when I finally write that post on my tinder experiences. So here it goes.

This experience actually happened about a year ago exactly – it occurred in August. I had been down on my luck with both boys and work by the time August came around. I had been working at Sears (shittiest job ever) and they gave me ZERO hours the one week. So I looked for another job and got hired at my current one early on in the month.

I had started the month off kind of messing around with this one guy – he had an interest in me, but even though I tried, I had none in him, at least not sexually or dating wise. So after hooking up a couple times, I ended it with him, and we still talk every now and then – as friends.

Right around the time I ended it, I got back into the tinder dating game, and wound up matching with this local guy named Brent. He was different from my usual types, cute, but not someone I’d normally go for. However, he seemed nice, and I wanted to be with someone local, so I agreed to meet him up for coffee the next day after we started talking.


Coffee was nice, he even paid for mine (which I wasn’t expecting). And we sat and talked for awhile and I found out he actually knew a guy I went to high school with (Andrew). Thinking it was worth giving a try, I saw him again. We went for a couple walks, and after the third? time we hung out, we went back to his apartment and I got to meet his roommates. His one roommate, John, was actually an adviser at my internship I had on campus. So I felt comfortable having those connections. And his other roommates were a couple named Ed and Cat, and they were nice to me.

We started hanging out almost everyday – I’d come over and we’d watch TV with his roommates or play video games. Drinking was involved sometimes. It was a lot of fun honestly. But something was lacking between Brent and I romantically. He walked me home the one night and when we were close to my house I’d start to do the goodbyes. And he asked if he could kiss me. I’ve never had a guy ask that, and it through me off. So I said “sure,” but it was still weird when he did actually kiss me. That was the first time, so I brushed it off. Let me also explain that there was a time and a place I kept my dating life a secret from my mother, so unless it was serious, I didn’t want to talk to her about it. So the less she knew, the better I thought.


A week went by, and we started approaching my birthday. Which he actually took me out for and it was really nice. He actually bought me a bottle of my favorite bubbly (because I mentioned it the one day). Then we went out to eat, and went out for drinks with his roommates that night. It was a lot of fun! But when I went to leave, I think he expected me to kiss him. And I probably should’ve at least done something. But everything with him was awkward for me that way, and I tried to avoid that. I didn’t want to kiss him – I liked him, and appreciated what he did for me, but I wasn’t into him like that. And I tried so hard to be, but every time that situation approached, I backed off.


This went on for about three, three and a half weeks. The last time we actually did something together, we had gone out for drinks and played some pool. Andrew (our mutual friend) was doing an open mic at one of the local bars, and we watched that. It was a good night – I always had a lot of fun hanging out with Brent, I felt comfortable with him. I remember we were standing there watching Andrew and he was like holding me. I tried to go with it.

Afterwards, he was walking me home, and my one flip flop broke, making it pretty difficult to walk home. So he gave me a piggyback ride about halfway there.  When we were right near my house, he asked me if we were steady now. I kind of went “I don’t know,” and shrugged. And he seemed disappointed but went “okay,” and we left it at that.


We’d been together for three weeks, and every time he wanted to kiss me, he would ask. And I know he probably was trying to be sweet and not intrude, but I even told him to stop asking. Because asking makes me think, and if I think then I don’t want to. It was awkward for me.

Around that last week, a guy I had been talking to a month or so before (Mat, the first Pittsburgh guy) hit me up again and we had been talking again. It wasn’t anything romantic yet, I was with Brent and I’m not the kind to do that sort of thing while I’m with someone else. But I had started telling him that I didn’t think things were working out with him, and he had been the one person supporting my decision. He understood everything I was saying, and it made me realize that I wasn’t being ridiculous knowing that there was no passion here. You can’t date someone just because they’re nice if there’s no attraction there.

Now here’s the good part. Up until this point, I had thought he was a good guy, nice and fun. So I felt like he would understand when I told him that I just didn’t have romantic feelings for him, but I did like him. Wrong.


He blew up on me. I had told him over text that there was something I wanted to talk to him about, but I wanted to do it in person. And he knew something was off, so he told me to just tell him. And I did. I told him that I had a lot of fun hanging out, but I just didn’t have romantic feelings for him. He took it personal. So personal. He threw in my face how he spent money he didn’t have on me for my birthday (never asked him to), and how he knew I was conflicted but wanted to give me my space and time so I could eventually come around (I don’t believe in waiting on something that’s not real – I’ve had sparks before, and I wanted that). And then he told me he should’ve known because I never felt truly comfortable at his place because I always kept my purse by me. Like so? If I’m drinking, I like having my purse within reach so I don’t forget it anywhere. It doesn’t mean I don’t feel comfortable…


But the kicker for me was when he said that we had a moment on the couch the one night – we did. And he said I didn’t attempt to do anything. Like it was up to me to make the move, not him. That he had been done asking me, it was up to me. I told him not to fucking ask me, to just try. So we spent a good amount of the night just arguing and disagreeing with each other. He made me out to be this bad guy for not wanting to keep it going. I said I still wanted to hang out, but just as friends. Nope, I’m the bad guy. Mind you, this was less than a month of hanging out, and we had barely kissed much less anything else.

So I gave him a few days to cool off. He was upset, I got that. I’ve been burned before, and I felt bad about ending it, but it was necessary. He was just blowing it completely out of proportion, and that wasn’t on me. Mat also agreed with me, and it gave me a bit of piece of mind about it. I was being realistic. Better to end it now than later.

A few days after this happened, we talked a bit and agreed to meet up. He said he did miss talking to me, and I wanted to try to work something out so he wasn’t so upset – you’d think we just ended a serious relationship with how he was acting. The day we met up was actually the first night I was going to meet Mat (who was driving up to see me). Things were over with Brent, and here was a boy who wanted to see me and who actually connected with me. It was fast, I know, but it was just how things timed out.


Anyways, Brent and I meet up, and we talk a bit and I explained how I was upset he felt that way – I really was, I even cried a bit over it because he made me feel so horrible. And he eventually said he was fine with us hanging out again, but it was up to me to plan it out and stuff. We sat in silence for awhile and I explained I had plans in a bit (they weren’t until later on, but it was so awkward I wanted to leave). He said “fine” and we parted.

Here’s where it gets good again. We spent the next couple of weeks kind of talking about meeting up but then I would back out. It was never a set plan, more like “hey do you want to go for a walk later,” and I’d go “hey, maybe!” and then be too tired. But then a part of me didn’t really want to go either, because it was just… awkward. And then one day he blew up on me again because he asked me if I wanted to hang out two days in a row, and the one night I backed off because my friend who lives in Pittsburgh was visiting and wanted to hang out (I hadn’t seen him in months). And the next morning I told Brent that if he wanted to hang out that day it was up to him.


So he blew up on me again going all “I’ve been trying to, how is this up to me?” yada yada. And I got so sick and tired of it. Then he accused me of dating someone else (not that it was any of his business at that point) and lying to him and other shit. It was overkill for me. Friends don’t do that, and that’s what we were trying to be at that point. And then at the end of his rant he goes “I’ll be free around 4pm if you want to hangout. I won’t be free later.” and I just kind of said “okay,” and let it go. Because what the actual fuck? Too much drama trying to make that happen.

The worst part is I got upset over the entire situation. Like it was my fault for not giving up faster or something. I thought three weeks was a good time to decide if it was worth moving forward or not – we hung out almost everyday so it was plenty of time to know if I was romantically interested. And I wasn’t, and I felt so guilty for not wanting to continue it. But his attitude when he blew up on me, I realized, was exactly why it didn’t work out. I have a good sense about people, and I knew there was something off, I just didn’t know what until he did that.


My lesson from this experience is to go with my gut on people. I know if there’s an attraction there – I apparently had more experience with that than he did. There has to be something there in the beginning for it to even grow. Similar to what I have now. Ray doesn’t exactly give me butterflies, but I feel happy and content with him – and we have chemistry.

When I had met Mat right after ending things with Brent, we had this connection, and he did actually give me butterflies. I think because he truly understood how I felt, and that built that intimacy for us. It’s still a shame to me that it didn’t work out, but that was all on his end, not mine. I wanted to wait and work it out. He met someone else and had 1001 excuses for why he couldn’t make it work and how I deserved better. Oh well.


Brent was by far my most complicated dating experience. Not funny like my previous post, but still hella awkward. I was starting to feel stuck until I ended it. It’s just a shame we lost even a friendship because he couldn’t handle it. He didn’t understand. And I tried so hard to make him see what I meant. That’s all I could do.

12 thoughts on “My Awkward Dating Experiences Part 2”

    1. Right? And I wanted to try to be friends with him because we did have fun hanging out. But he talked shit on me to his roommates and then put me in an awkward position like that. The last time was it for me, I gave up.

      Liked by 1 person

      1. It honestly seemed like it at that point! He even told me he was fine with waiting until I got to that level with him, which seems nice, but it never would’ve happened. I’m glad I gave up on him, too, it was just bad.

        Liked by 1 person

      2. Ugh, if I felt like someone wasn’t moving at the same pace as me emotionally wise I would not pressure them to catch up… even though he said he would “wait” I feel like I would feel so much pressure to brew up feelings for someone that just weren’t there. Oh nooo…I feel bad for who ever ends up with that guy, lol.

        Liked by 1 person

      3. That’s the thing, too, there was no spark or attraction, and it’s kind of hard to make things move forward without that. So yes, I could’ve stuck it out and tried harder – but the end result would’ve been the same. It never would’ve worked out, and I tried so hard to explain this to him and he apparently could not get it.

        It would’ve been a lot of pressure to be further in and still lacking feelings. And he would’ve gotten even more attached, and that would not have been fair. But he made me seem like I was terrible for being realistic lol. He just couldn’t understand my point of view. I feel bad for them, too, but I hope he gets his act together.

        Liked by 1 person

      4. Yeah, exactly! Even if you kept trying w/him, the sparks weren’t going to just start flying out of nowhere. He wanted to be w/you so bad, that’s why he couldn’t get it…poor guy, hope he gets his act together, too! At least he’s out of your hair now! 😊

        Liked by 1 person

      5. Exactly! They never would have. You can’t force that kind of thing, and you shouldn’t. I don’t like waiting around for something like that because I believe you know when you’re supposed to be with someone – you feel it. Whether it’s short term or long term, you know when you fit with someone. Brent and I never clicked.

        And I felt bad, but if anything I learned from him that you can’t make something happen just because you want it to lol. It’s been about a year now so I’m long over the drama from him, but I’m definitely glad he’s out of my life after that!

        Liked by 1 person

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