dinner, drinks, and disastrous dates

Online dating is portrayed by online dating sites and apps to be fun, flirtatious, and a great way to get to know people. While it can sometimes be these things, I regret to inform you that there are some really shitty guys (and probably girls) out there. I felt like it was necessary to put together a collaborative post that really encompassed some of the worst dates that myself and other bloggers have been on.

Here are just a few of the bad dates all three of us have experienced.


Mr. Catfish –

I’d been talking to a guy on tinder for a while. We had good conversation and it seemed like we had a great connection. His profile gave me a good idea of what he looked like; 26 years old, 5ft9, slim, dark hair, beard, tattoos, piercings. All seemed great!

After a while we decided on a time and place to meet up for our first date! I was super excited. We’d agreed to meet up at one of my favourite bars at 6pm. I’d spend an hour getting ready, put my best dress on, had a couple of glasses of wine & off I went… an hour early.

It turned out that my friend would also be at the bar that night so I felt a lot more relaxed and slightly embarrassed that she’d be there peeping over at me on a first date. I’d had a drink with her at the bar as I had an hour to kill and when it was approaching date time I went and found myself a table which was right opposite the bar area.

Sitting there nervously it had hit 6pm and there was no sign of him. Trying not to be an eager beaver I thought I’d give him another 10 minutes to see if he would appear. Nothing. I kept scanning the room to see if I could see him & then I received a text. “Just getting off of the bus, will be a couple of minutes” AHHH FINALLY.

I quickly dashed to get myself another pint of Bad Kitty and ran back to my chair. Trying not to stare at the door to see him walk in I kept my eyes straight, watching people coming and going from the bar. A few more minutes had passed when all of a sudden a man who had been sat at the bar since I’d arrived turned around with 2 pints of bad kitty in his hands, smiles and locks eyes with me. He pops a pint in front of me and says “Oh, I knew you’d have good taste in beer!”… then takes a seat. Thinking to myself “who the hell are you?!” I sheepishly said thank you and felt eyes on me from my friend at the bar and then my phone buzzing with numerous texts from her.

I politely asked “sorry, do I know you?” With confidence, he says “Yes, very well actually. I’m Dan, from Tinder. I’ve been admiring you from afar and I love how your back curves in that beautiful dress of yours” and then ran his hand down my back. *CRINGE*

I’D BEEN CATFISHED!!!

catfish definition

He’d been sat there the whole time, watching me, listening to me. The guy who I’d seen in the pictures was not the person sat at the table with me. He was about 6ft5, very large, I’d say in his late 40’s & bald. Trying to stay polite I explained that he looked NOTHING like he did in the photos on his profile and how worrying that was for me.

I quickly took myself off to the toilets where my friend followed me and we burst out into nervous laughter and tried to plan my escape. She told me she would get some shots in for us at the bar and then we would tell him that I’d been called into work and I had to go and catch the next bus.

I had no intention of catching the next bus.

I returned to the table and explained to him my excuse to leave. But I felt terrible for him!! I felt like a horrible person but I couldn’t stay. He told me he would walk me to the bus stop. I declined a few times, but he still followed me making comments about “my beautiful figure” and asking questions about where I worked and lived. I said goodbye, got on the bus, explained to the driver that I needed to get away from someone and went two stops.

When I got off of the bus I was sneaking about trying to return to my friend at the bar, praying I didn’t bump into him. I’ve never felt so uncomfortable. Once I made it back to the bar and my friend and the bar staff cheered and we proceeded to have a brilliant night.

I was absolutely devastated and ended up feeling really shallow. I had just ditched a guy in less than 5 minutes on a first date.

At the end of the day he had lied to me, creepily ran his hand down my back, made comments that would make anyone shudder & followed me when I had declined. Not a great first impression really?!

Needless to say we didn’t have any contact again.

— Brook @ beaside.co.uk


Mr. Sexually Obsessed –

My goodness, this was an unexpected one. Things actually started off well. We were just meeting for drinks, dressed for the occasion, I was excited. I looked bomb. On my way there, I called him to let him know I was on route. He tells me he’s hungry, Sigh. We hadn’t arranged for food?! I had already ate so thought this wasn’t the best turn out for me. Nonetheless, I won’t be selfish. He eats, I reluctantly have a plate of chips in front of me that I barely touch. He was polite and generous, as I said things started off somewhat well.

We head off for drinks, and it was on our second round that things took me by surprise. We were all cosied up in our blankets on the heated roof top garden, sipping away at our cocktails, discussing business and such things. It was a comfortable hand on leg vibe. I’m fine with that. Out of nowhere, I get asked when the last time I had sex was? My response ” Excuse me?!” He seemed quite shocked by my abrupt tone. Perhaps I was flirting beforehand, led him on and so he took the plunge in asking what he thought was an appropriate question. Who knows.. but I was so taken aback by it, of course I was going to think it was too much. I wouldn’t tell him anything.

We went back to talking about business and such else. Then again, abruptly, he passes comment on my lips, and how small they are. My instant response, ” I know how to use them pretty well though” Perhaps looking back, this came out more flirtatious than the guarded approach I was going for! Then he asks to kiss me. Who f******* asks this, I thought. Of course, I told him no. “You just insulted them, what makes you think you deserve this.” Writing this, I realize it sounds quite aggressive but it was all said light heartedly with a grimace upon my face. I think although his questions took me by surprise, I weirdly found it refreshing. Having just come out of a long-term relationship, flirting wasn’t unwelcome as it became a distraction, nor was it an issue for me to portray. I guess I warmed to him after this because I seem to have gave him the benefit of the doubt and stayed for a final round.

However, looking back I realize the conversation that followed was completely inappropriate and I feel like I was in a very vulnerable place, mindfully. Hence, a worst date, for sure. This guy definitely needed to hold back the reins with his very dissolute approach.

Mr. Self Absorbed –

This speaks for itself really. Again, drinks. Admittedly, I was late.. a whole hour late in fact. Nonetheless, I was very apologetic about this and offered to buy him a drink. (Already on his second round having waited so long, so he graciously declined the drink) This guy didn’t ask me anything about myself. He spent the whole time reminiscing over sports games he’d partaken in, injuries, his favourite teams etc etc. It was exhausting to listen through. It’s actually quite heavy chat yano! Sports and such. Actually, I am quite the listener and I remember myself really trying to get involved, motivating him to follow his dreams. Then I lost interest as he wasn’t bouncing back the motivation.

I began to just sit back and analyse him. I let him do the talking I guess, all I wanted him to do was ask me a question about myself, but nope.. he chatted and chatted and chatted but all about himself. I remember at one point saying “ You can tell you live and breathe your sports, it’s ALL you talk about” Emphasis on ‘all’, of course. Yes, this was a hint. He was supposed to acknowledge this and have a self-awareness moment. But he didn’t. I got the impression he was no longer interested in me, and suggested we split the bill and went our separate ways.

Later that evening, he tells me he found me quite intimidating and thinks that that’s why he had spoken about himself a lot. I made him nervous I guess, so his response to that was just keep chatting about something he knew and loved.
Next time I see him is in a club on a night out. Was it awkward? Yes.

— Sasha @ alwaysobsess.com


Mr. Escape Artist –

Have you ever matched with someone online that you had so many failed meeting attempts with you assumed you were never going to meet in real life? This contender was one of those guys. We texted for so many months with him continuously bailing on me I started to make jokes about him being a Catfish (sorry Brook, I know it’s not funny!).

We eventually met and had a decent time. I was a little iffy about his personality but after discussing it with my girl friends they told me I should give him a chance. “You never know what could happen, Steph.”

So, I went to see him a second time… followed by a third. The third night we hung out things started to get a little heated at which point I told him I did not want to take things any further than just making out as I wanted to actually get to know him first. Plus – he had ditched me so many times I thought it was only fair for myself to really pump the brakes on this one. He was obviously annoyed but he said okay and we went to sleep.

To my surprise, the next morning I woke up and he was already gone. This is something you see in movies or hear about from your guy friends – they don’t like the girl so they leave them in the middle of the night or whatever… except I was AT HIS PLACE!! I remember thinking it’s so weird he left me here alone… we pretty much just met. Trying to give him the benefit of the doubt, I waited around for a little bit thinking (hoping) maybe he was actually a nice guy and went to pick up coffee or breakfast. But then reality kicked in and I realized this guy was not coming back home. I got my stuff together and left – we never talked again!

Mr. Black versus White –

I matched with this tall, very handsome, and seemingly intelligent guy on Tinder. I do have to note for purposes of the story that he was African American – like I said, strictly mentioning this for the story. We messaged back and forth for a couple days. The conversation felt like it was flowing very naturally and he had proven to be a very intelligent guy, something that I find extra attractive in a man. So, when he asked me if I wanted to grab dinner after work one day during the week I quickly said yes. I’ll be honest, the next few days he was texting me a little too much – like sending way too many messages before I even had time to grab my phone to read his texts, which made me a little annoyed but I was still excited to get to meet him in real life.

Into the first few minutes of the date, I had a really good feeling about it. Once again, our conversation was flowing really smoothly and we were not having a hard time coming up with things to talk about. In my head I was like omg omg omg omg omg – finally a good one.

He asked me my political stance, which I can only assume was due to the fact that Barrack Obama was our former President and Donald Trump is a racist (sorry to any Trump supporters but it’s true!!). I was surprised that he was fearless about bringing up politics because it can be a touchy subject.

See related post: Politics and Dating

While I am aware that being an Obama supporter is not a public declaration about being or not being a racist – I was very taken aback when further discussion led to him making multiple comments suggesting he believed I felt superior to African Americans!!! If he had listened to anything I was saying, he would know my current job is a position in which I am heavily advocating for minorities and fighting against social injustice. After multiple attempts to explain that I was definitely not a racist, I politely told him it was time for me to go home. He reached out to me a few times over the next week until I told him I was not interested in going on another date.

Mr. Best Buy Guy

Honestly, I couldn’t think of another clever name for this guy but he worked at Best Buy so we are going to call him Best Buy Guy. This particular guy I was actually extremely hesitant to meet IRL. He was horrible at holding conversation through text, but he kept asking me to grab drinks with him. I told myself you need to just give him a chance so I went out for drinks with him.

While we were out for drinks we actually had really good conversation. I was surprised but I guess some people really just don’t communicate well through the phone or online. We had a few rounds of drinks and he ate dinner (I wasn’t hungry) and then he declined when I offered to split the bill. We kept talking for a while – we had to have been there for at least 2 hours – and then I said I was going to use the restroom. When I came back from the restroom, he was GONE. I thought omg not this again.

He messaged me very shortly after saying he doesn’t know why he left, he just got nervous, and asked if we could meet up again sometime soon. I think it goes without saying that I did not see him again.

— Steph @ stephandthecity.org


I think Brook really said it best:

When I sit and think back to my online dating days I remember the majority of it quite fondly. I had some lovely dates, fantastic nights out & my favourite part, gained some amazing friends. On the flip side of it I had a small handful of not as nice experiences. Being stood up, lied to & sexually harassed.”

Although not every date is a bad date, sometimes you do have to kiss quite a few frogs before you find your prince.


If you have made it this far – first and foremost, I hope you enjoyed this post and laughed a little too! Secondly, please, please, follow these amazing ladies’ blogs! They were fantastic to work with and I really enjoyed working on this piece!

For those of you who are currently online dating or have online dated in the past: what is your worst dating experience? Leave it in the comments below!

With love from all of our cities to yours,
xoSteph, Brook, & Sasha

8 thoughts on “dinner, drinks, and disastrous dates

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