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From Hope to Nope | Dating Disappointment While Single | Episode 50
Episode 5011th August 2026 • All About Being Single • Wioleta
00:00:00 00:14:24

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Disappointment in dating options is a common theme we dive into today, and let me tell you, it’s a real doozy. We chat about the struggle of being single and the rare moments when you actually meet someone who sparks your interest, only to face the letdown of a last-minute cancellation or a total dud. I mean, how many times have we thought we found a gem, only to realize they’re just another rock in the dating landscape? I share some personal stories that highlight those frustrating encounters, like that guy who flaked after a great connection, or the one who thought sending me money would win me over—spoiler alert: it didn’t. So, grab your favorite drink and join us as we navigate the wild world of dating disappointments and maybe find a little humor in the chaos along the way!

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Dating can sometimes feel like a game of musical chairs where everyone is dancing around, but when the music stops, you're left standing alone. In this episode, we dive into the bittersweet realm of modern dating as I, Wioleta, share my own experiences of disappointment while navigating the single scene. It’s a wild ride, filled with moments of hope and letdowns that are all too familiar. I discuss the frustrating reality of meeting people who seem promising but then vanish faster than my motivation to go to the gym after the New Year. Picture this: you finally meet someone who ticks all the right boxes at a bar, you exchange numbers, and then—bam!—they flake out. I mean, what’s up with that? It’s like finding a unicorn in the wild, only for it to gallop away just when you’re about to take a selfie. Throughout our chat, I also reminisce about some awkward encounters, like that one guy who tried to buy me a drink from across the bar. Spoiler: it didn’t go as smoothly as I’d hoped. It’s a reminder that just because someone shows interest doesn’t mean they’ll make a move or that you’ll be interested in them back. As we peel back the layers of dating disappointments, we also talk about the importance of reframing these experiences. Instead of wallowing in self-pity, I encourage you to look at each encounter as a step toward figuring out what you really want. It’s a journey, folks, and every twist and turn teaches us something new about ourselves and what we’re looking for in a partner.

Transcripts

Speaker A:

Is disappointment in your dating options part of your single era? Welcome or welcome back. I'm your host, Wioleta, and this is all about being single. So today I want to talk about just something that's.

That I find incredibly disappointing about being single at times, and that is just how rarely you actually meet someone that you're interested in when you're out. You know, there's this constant narrative that if you're single, you just need to go out. And I do put myself out there whenever I'm able to.

And then every once in a while, I do meet a guy. And the last month, I actually have met, like, three potential people. But then, like, nothing happens.

And sometimes I feel like I'd rather just not meet somebody than meet somebody and just be disappointed. Especially because it's already so rare for me to even meet men while I'm out that are actually single and that are ones that I'm interested in.

So especially when you meet somebody that you're interested in, and I think comes of it, it's like, oh, my God, just so extra disappointing.

And because I hardly ever meet people, I think that disappointment becomes even larger than it would be if I was constantly meeting people out and about. But also meeting a man and meeting a man that I'm actually interested in, that's the other part of the problem of this.

Those are two very different things. And sometimes, you know, I get dropped some people, but then they're just not people that I'm even interested in.

So that's the other part of what sucks about, you know, being single. As you, especially as you get older, I feel like, because you have fewer opportunities to even meet people.

So when I was out for work in a different state, I went out one night and met this one guy who started talking to me first. He was, like, 35. I actually thought he was way younger at first, but he was there with his friends. It was one of his friends, like, birthdays.

And so we talked for a little bit. Then I talked to, like, his friends, and then there was another group of people there that I ended up, like, talking to.

Those guys were out of town for, like, some hockey child conference. I don't remember fully, but that's beside the point.

Anyhow, I was very proud of myself because I did find this guy to be cute, and definitely none of his friends were interesting to me. So towards the end of, like, the evening, I, like, made sure to talk to him some more. And then I gave him my phone number.

Well, he's gonna give me his phone number. I just gave him mine and we were supposed to hang out the day after. And I honestly wasn't even thinking anything was gonna happen.

Like, I was kind of thinking, oh, he's probably not even gonna remember. Or my name starts with a W. So sometimes I'm like, oh my God, this person might probably not remember like where my name was.

Anyhow, he ended up like, I'm at work on Monday, he ends up texting me. And so we literally end up talking and we're supposed to hang out that evening. And then of course this douchebag doesn' cancels like last minute.

And it's just, it's disappointing. Like, either way, I'm very proud of myself because I normally don't try to like make moves of any kind. Like I prefer the guy to make the moves.

But I was just kind of like, okay, it doesn't even matter. This guy doesn't even live out where I live. The stakes are a little bit lower.

But that was just, it was just extra disappointing because like the entire day I'm thinking we're actually hanging out and then we don't end up hanging out. So it's just, it's just disappointing. Like, I hate flakes. Fucking hate flakes.

I just was excited, you know, because this was going to be my first date in a very long time, honestly. So again, I think that disappointment sometimes becomes even more of a disappointment.

And then there was a time when I went out to dinner at a place right by my house and there was a guy across, sitting across the bar and I like looked at him, I smiled a few times, so, you know, trying to show him that I'm interested. He never approaches.

But then there was another guy, an older dude also on that side, who I was definitely not interested in, who ends up giving the waitress money towards my bill. I've never had this happen to me. It wasn't like he bought me a drink and it was just weird because it's like, hey, please.

I, I definitely didn't want to talk to him and be proud of me, cuz I think an older version of me would have just felt bad for the guy and would have just walked up and talked to him because he decided to send this money. But the new version of me was like, I, I'm not interested. Like I'm just not interested. And I don't even. Here's the other part of it too.

I think it was awkward that he sent me money.

I think if he maybe if he had asked the waitress for her to maybe even ask Me if I, you know, if I'd be willing to speak with him, something like that, I'd be a little bit more willing to do that because then that just shows some kind of guts.

And you're not like almost trying to buy me in a weird way and then expecting me to kind of make the move, you know, because then he just kept on like staring at me to see if I was going to come by. And towards the end I like, I was trying to give the waitress the money back and she was like, well, you want to give him the money back?

So she made it even more awkward, like oh, I'm not supposed to be doing that and I didn't want to embarrass the guy. So there is also that obviously. But like I didn't want to take the money cuz I'm not also going to go talk to you.

So it's just, it was just such a weird situation. But again, the person that I was interested in didn't even make any sort of a move.

And then there was another time I walked into this brewery by my house and there was a dude that was already sitting there and I walk in and he starts talking to me.

He was nice at first, but then just like the way he works in finance and he just seemed very like salesy and it just felt like all of the stuff he was talking about just felt like he was selling himself. And it just, I right away knew like, hey, this, this definitely isn't something I'm interested in pursuing further.

And I mean I spoke with him and you know, overall the conversations weren't bad. There was good parts of the conversation. I just knew, I, I just know pretty well like what I can handle.

And he just seemed very, I don't know, like one of those people that almost like feels like they just lecture at you instead of having a conversation. That's kind of how I can describe it. So there's definitely no chemistry.

And you know, I can't force myself to be attracted to someone just because they're technically available and interested in me and I'm technically available.

But yeah, so like there's so many times when you might be single, especially nowadays I feel like I, you know, see this and hear this from more people who are single, especially as we age. Like the person who likes you isn't necessarily the person that you like.

And I know that's been a thing forever for everybody, but sometimes the person that you like doesn't make the move or you don't make the move, you know? Then everybody just goes home and is still single. You know, a few things that I want to mention.

It's like the one guy that I met when I was on my work trip.

It's like, I'd rather just not have you text me and then give me some kind of hope that, hey, maybe we can meet up and maybe something can come of this again.

I didn't necessarily think anything much was going to come out of it besides a good evening, but either way, I'd rather not have you, like, mess with my hope for something and then just screw it up. Like, he did not have to text me at all that morning. Like, I wasn't really expecting him to do it.

So it's very odd that, like, you're going to do it and then you're going to back out last minute. And so, like a hill that I'll die on is.

It's incredibly rare to find someone that you're mutually interested in, that there's mutual attraction, mutual availability, just that the timing aligns, that the effort is also similar, that the compatible, that the compatibility is there. Like, it's just very hard. Like, I feel like most people legit do settle because it's so hard to find all of those things.

And never again am I going to treat someone's minimal interest like a potential relationship. Because I think sometimes it's easy to do that when you're single.

And again, especially when you're not meeting a bunch of people, you know, you can kind of like hyperfocus on somebody. You know, if somebody texts you after meeting, okay, somebody flirts with you, okay, maybe, you know, somebody says they should see me again.

Okay, interesting. We'll see if it happens. You know, me don't say that obviously, to them.

And I'm not trying to say to, like, lose hope, but I think just being a little bit more realistic about things. You know, there's no actual plans that happen. And you're not actually dating. You're not actually dating.

Like, they don't really mean much until things are actually truly happening. You know, I love to dance. So we're going to do a little dance break.

We're not going to do a note to self today, but just go ahead and dance with me and we'll come back and continue on with the episode. And so, like, the no like to stand. And for me today is those people who have met their significant others and have only dated one or two people.

And basically by dating, they meant, you know, they literally, after the first date, became got into a relationship with that person and didn't continue on dating. Like, this is what the dating world is like. So you have no lack to stand and tell me what I should be doing differently.

You know, why I'm still single when, like, there's a bunch of flakes out there, there's a bunch of people that you know you're not interested in that are interested in you and vice versa. And it's. It's not so clear. It's not so black and white. I'm not going to accept a date with every man that I'm in that shows interested in me.

And I'm also not going to, like, I'm allowed to not be interested. They're allowed to not be interested. You know, I'm allowed to meet someone and think, nope. They're also allowed to do the same.

But also because, you know, we're older and we know exactly what we're looking for, it is even much harder now to find somebody that's compatible. If you met somebody when you were like 20, you really didn't know about all these things.

You just went along with dating people because, oh, hey, I'm. I like this person. They like me. And things get way different when you truly start knowing what you actually want in this life.

And that's why it's so much harder, I think, to even get into a relationship as you get older. If you have any stories about just like dating disappointments, please feel free to go on all about being single dot com.

There's a spot for you to send in a voice note. So do that and send that in and let us know how disappointing dating can be. And we're going to finish off with the glow up.

So I think my glow up for this episode really is just about changing the way I and you look at these interactions. You know, I think it's easy to think another guy where nothing happened.

But honestly, I think sometimes it is a good idea to look at those things differently. It's a fact of, okay, there were people that I was able to meet.

So there are people who are single who are out there, who are going out, and I put myself out there, and that's important to me.

And I had a few conversations with these people and I figured out whether or not I was interested in them, and then I figured out whether they were capable of following through.

You know, even with that guy from when I was out of town, like, old me maybe would have checked in with him, like, when he wasn't responding to, like, exactly where we're gonna be meeting. Old me would have just been like, okay, what's going on? And I'm glad that Numi is like, no, no, we're gonna. We're gonna see who this person is.

Like, we're gonna see if they can follow through on plans, because I need somebody who follows through on plans, and I don't want somebody who only does it because I'm, like, reminding them, like, that's just not the kind of person that I want to date. And he showed his true colors, which was perfect.

And so basically, the work trip guy showed me that texting me isn't the same as actually going on the plans. And then the guy who gave money towards my bill reminded me that someone being interested in me doesn't mean I have to be interested in them.

And then the guy that I liked who didn't make a move at all reminded me that my attraction doesn't automatically create reciprocity, and that's okay. And then the sales pitch guy reminded me that I know pretty quickly when someone's energy just isn't for me.

So I think the glow up really is just looking for the.

The good and the disappointments, trying to figure out what that disappointment is teaching you and trying to reframe it and trying to figure out, okay, this is why this didn't happen. You know, there's got to be a bigger reason for why that didn't happen and why that's a good thing at the end. So try to do that with yourself.

Think about any dating disappointments that you have been through or just any disappointments if you haven't really been dating in a while. So maybe even the fact that there is a lack of options. You know, think about how that's actually possibly a good thing for you at this time.

So I do want to let you guys know that I had to record this on my phone because I want to record this this morning and the Pog Trek. So it's like this thing that I use to record my episodes with that a lot of podcasters use to record episodes with.

It's saying that my card is full, even though I've deleted a bunch of things. So I don't know what's going on. I think I got to get a. A new disc to record these on. So I am recording it on my phone.

So if the quality is a little bit worse, I apologize. But anyhow, thanks so much for listening to me, as always. Even if we're late, we're right on time. I will talk to you next Tuesday. Myself.

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