Overbooked and Caught Red-Handed with OKCupid

February: the worst month of the year.  Seeing as this was the month I decided to join OKCupid, I was basically just setting myself up for a month of dating failures.

In the first week, I scheduled three different OKCupid dates:
1) Wednesday with one of those guys whose profile picture is him with a dead fish he just caught (that should have been the first red flag)
2) Monday with someone who was completely not my type but played at my weakness for food by offering to take me out for food on the first date. (I ended up cancelling this and never rescheduling.)
3) Wednesday with a guy who looked really attractive in some pictures but balding and only semi-attractive in other pictures – but still really funny nonetheless.

For the first date, I hopped in an Uber and met up at the same place I had gone on a second date with the anesthesiologist.   The bar wasn’t that crowded except for a few couples and some guy that went nuts when his college basketball team won at the buzzer.  Here is how it went down…

Problem #1: Juan Pablo Syndrome

You know when you are talking to someone and the entire time you can just see them waiting to start talking again?  Well, not like this guy gave me many chances to talk in the first place, but when I did, he was practically jumping out of his chair ready to start talking again.  I could physically see himself trying to stop himself from cutting me off (which he still did quite a few times).  And when he was talking, I honestly can’t even remember what he was talking about.  All I can tell you is that when he did go silent, he wasn’t listening – he was just waiting to talk.


Problem #2: Total Bro

Again, there isn’t much to really say about this except that when you see/hear/talk to a Total Bro, it is obvious.  To add to his bro-ness, he continually kept referring to his friends as “my frat brothers.”  I’m cool with the fact that you were in a fraternity in college, but kiddo, you have been graduated for at least 5 years now.  It’s time that you just call them your friends now…or at least when talking about them to someone you just met.

bro dance

Problem #3: Dull

When a guy has JP Syndrome, he typically isn’t dull at the same time.  Well apparently it is possible because boyyyy was he boring.  No joke, my brain went into sleep mode the same way a computer does.  I completely stopped listening to what he was saying and just smiled, nodded, drank my beer, and thought of other things while he went on and on about absolutely nothing interesting.  I got away with this because – in true JP Syndrome fashion – he never asked me about what was on my mind.

fake smile

About halfway through the date, I checked my phone and had a text from upcoming Date #3.  It read: If you don’t think I’m gonna comment on this, you’re mistaken.  Assuming he must have been talking about a text I had sent earlier, I asked him what he meant.  Then I went back to my date…

Problem #4: Inconvenience

Usually when someone wants to meet up anytime after 8pm, I find it to be pretty inconvenient because I usually have to go way out of my way to meet him.  But this first OKCupid guy lived not too far from me, and so I didn’t mind going out with him later in the evening.  The inconvenience factor kicked in around 11:15.  Both of us had finished our drinks and not only was I bored and hungry, but I was also just plain exhausted.  I told him that I wasn’t trying to cut the date short (even though we’d already been out for about 3 hours) but that I had to get into work early the next day and would need to head home soon.  He said, “Well, I was going to have another drink, soooo are you just going to make me drink it alone? You can just have a water or something.” Ummm, seriously?  I said, “It’s not that I can’t handle another drink, I’m just really tired and need to get some sleep.”  His response? “Well I’m going to have another one sooooo I guess I’ll have it by myself.”  Honestly, I should have just left.  But I asked for a water and stuck it out a bit longer until he finished his beer.

fucking kidding me

When he went to the bathroom again, I whipped out my phone to see the following response from upcoming Date #3: I mean, aside from that being a lovely leopard print shirt, I may just leave it at that.  Oh fuck.  Caught red-handed.  It was time to get out of there.

Problem #5: First Date Check

Call me old fashioned, but I do expect a guy to foot the bill on the first date.  Now, to clarify, if we happened to have a massive dinner or racked up a gigantic tab, then of course there are times when the girl should help out.  Similarly, if it’s a second date, then who pays the bill is not a huge deal anymore.  Despite this expectation, I will still make a quick I’m-expecting-you-to-say-no offer to pay, and many guys know the drill and tell me that they’ve got it covered.  OKCupid Date #1 was not one of those guys.  I made my fake offer and without hesitation he said “sure, let’s split it.”  I typically won’t get too overworked about this, but I was tired and felt forced there longer than I wanted to be…and I had less to drink than him.

you are really serious

I am sure it comes as no shock that I never saw OKCupid Date #1 again.  But now I was super bummed about Date #3 seeing me with Date #1 because I legitimately was excited to go out with Date #3.  I didn’t know how to respond, and so I waited until morning to address it…


The Time I Picked Up a Guy at a Bar

Meeting guys at bars is a tough call these days. For me, when I go out,
I’m out with my friends and don’t want to spend my time talking to a complete rando unknowing if he is just trying to pick me up for a one night stand or not. Plus, I’m incredibly picky, so if the guy isn’t drop dead gorgeous and doesn’t have a perfectly witty pick-up/opening line, then chances are I won’t give them my time. As I said, I’m there with my friends to have fun, not network.

Flip it around, and guys don’t have it all that easy either. Their chances of a girl being receptive to him approaching her is 1 in 5. She will either think he is a creep, already have a boyfriend, not be interested, be having a girls’ night out…or will take interest in him. All in all, finding a match at a bar is increasingly difficult for everyone.

Early September 2013, my friends and I were having a Sunday Funday brunch at a local bar to kickoff the start of football season. Midway through the game, a group of guys were seated a few tables from us, and one tall, scruffy guy caught my eye. People weren’t mingling around at this bar, so I knew there was no chance we would cross paths and start talking. So before we left, I wrote my number on a napkin, went up to him at his table of friends, gave him my number, and then bolted. I imagine myself being incredibly awkward…but it worked! He texted me saying he was flattered and impressed by my boldness. We planned to meet up that week. Brace yourself, this is one of my few two-part tales.

approaching a guy at a bar

For our first date, we met at the bar around the corner from me. (Funny enough, this is the first first date I had here; it has since seen me have numerous other first dates, so I can only imagine what the servers think of me.) He was a bit better looking from far away, but hey, he wasn’t bad. Per usual, I still found flaws.

Problem #1: Total Bro
Right off the bat, it was obvious that this guy was a bro. One of the first things he told me was how that Sunday ended with him and his friends getting so wasted that he had to go into work an hour late. Honestly, I didn’t care so much about that because I can appreciate an aggressive Sunday Funday here and there. But – and yes, this is why I’m picky – it was the bro-ness in his voice when he told the story that just screamed “SHOTS FOR DAYS! I AM A BRO!”

total bro fist pump

Guess what? That’s the only major problem I found on that first date. Unfortunately, I didn’t feel any chemistry, but it was definitely worth another shot.

The First Time That Coffee Met Bagel

Coffee Meets Bagel has a similar concept as Tinder but limits you to passing judgment on only one person per day. If you like one of your daily matches and they like you, then you are connected through a temporary phone number that allows you to text for a week and potentially swap numbers to meet up.

Intro: the anesthesiologist. He was a bit short for my taste, but he had scruff and a great job, so I decided to give it a shot.

Problem #1: Total Bro
It’s hard to describe exactly what this even means, but when you meet a bro, you know. He carries himself in much the same way that a college frat guy does. A Total Bro in it’s worst form comes off as arrogant, drunk, dumb, and douchey. I have definitely met more bro’ed out guys than my date, but it was hard to deny the obvious truth: he was a Total Bro.

Problem #2: Juan Pablo Syndrome
The typical guy-talks-too-much issue. Fortunately, the anesthesiologist was actually decently interesting when he talked about his career and experiences with his career, so this problem was less painful than usual.


Despite these problems, anesthesiologist was one of the few guys who has made it onto a second date with me.