8 Awkward Dating Moments

For those of you who might not be in the know about all things online dating related, there are many more sites out there than just eHarmony and Match.com [full disclosure, I’ve been on Match in the past but not eHarmony since I’m way too lazy to fill out all those questions]. For example, I’m currently on OKC as well as an app called Coffee Meets Bagel.

One thing I like about CMB is that they come out with surveys and blog posts that are actually pretty interesting– take their latest post, which is on 8 awkward dating moments and how to get out of them. I read through and found these pretty amusing, since I think I’ve experienced all 8 situations at one point or another. I thought maybe y’all would get a kick out of reading my own personal experiences, mini-story style.

1. The Neighbor Make-Out Sesh
OK, so this has never really been an issue for me, maybe because Boston guys seem to not be super into PDA. But I WILL say that if it happens when you’re on a date with a guy you’re into, it’s just added incentive to up the ‘touching factor’ (you know– the hand on the small of the back, the hand on the knee, leaning into each other, etc.). When you’re on a date with someone you’re not into, it just makes things realllllly awkward.

For me, the worst thing is actually the Neighbor that You Know issue. Once I was out on a date at a local place I tend to frequent. The date went really well, and we were there for 4-5 hours drinking, chatting, and engaging in the whole ‘touching factor’. It was only towards the end of the night that I realized that 10-12 engineers from work were sitting right near us, and had been watching us the entire time.

NO. Not cool, guys. Not cool.

2. The “I thought this was just going to be a hug” goodbye
Ugh this has happened to me soooo many times. I go in for the hug and all of a sudden there’s lips on my face! It’s just really awkward for everyone involved. Guys, please get better at reading body language, OK?

Earlier this year I went out on a date with a guy who I actually kind of liked, but at the end of the night he did the whole go-for-a-kiss when I thought we were hugging, and it made me so flustered I didn’t know what to do. So I got weird. And he got weird. And we were both being weird. And it ruined the whole vibe of the date. And then he said he’d like to see me again so I said sure, you have my info- (as in, call me!). And he responded by saying, you have MY info! (As in, I should call him??) I never called him and he never called me.

Yeah, that was a STELLAR experience.

3. The I-think-I-kinda-know-you hello.
Thankfully this situation has never happened to me in real life, but only online before actually meeting up with the guy. A few years ago I went on a date with a guy while I was still in grad school. I wasn’t super into him from the beginning, but I figured- why not? [To put this in context, here’s an actual gchat I had with a friend about this very date: “OK, is it sad that when reading an email someone sent to me on OK Cupid, I’m more excited about the possibility of doing an impromptu ‘info interview’ with him than with the possibility of an actual date?”]

When he showed up, he didn’t really look like his photos (as in, the pictures were probably taken 10 years earlier). Strike one. Strike two was his messy eating– yes, he was a messy eater and it totally put me off my lunch. Strike three, he was just really boring. So we had our date and I declined when he asked me out again. Fast forward a few years later, and I was trying out a dating site called How About We… I was still figuring out how to use the site, and stumbled on a guy’s profile who seemed pretty cute. I ‘liked’ his profile, he messaged me, I wrote back. Then– it happened. He wrote to me and said ‘I think we went out on a date a few years ago’. Nooooooooooooooooooo.

I didn’t know what to do so I never wrote back to him. Ignore FTW!

4. The “Who are you again?”
So, CMB has this one down as you forgetting your date’s name halfway through the date. MY issue is forgetting which guy is which. When I’m not dating any one particular guy, I tend to have an average of two dates a week. As you might imagine, guys start blending together really quickly. I tell my dates I have really bad short-term memory but the truth is I’m lazy and I date a lot.

Once I actually didn’t know who I was going on a date with. Long story short, a few years ago I attended an Indian Speed Dating event for Valentine’s Day. Apparently I met some dude there and gave him my phone number. A few days later on Valentine’s Day, he called me AT WORK and asked if I’d received ‘his package’. I got really freaked out since he essentially stalked me to figure out where I worked… the package ended up being a rosebush which was kind of nice? I felt bad because obviously I’d made an impression, so I agreed to go out with him. When he showed up, I had absolutely no recollection of ever meeting him, and to be honest I think I was pretty buzzed when I gave him my phone number.

The date didn’t end up going well, but that’s a different story. (Also hilarious).

5. The surprise third-wheel.
This has happened to me twice, two different ways.

Story #1: The very very first time I ever ventured online, I was on Match. This cute guy started messaging me, and then we started talking on the phone. He eventually asked me out, and I said yes– but I was really nervous so I did the whole, we have to meet in public, during the daytime, I am going to tell my friends where I’ll be, etc. routine. An hour before we were set to meet, he called me and said he was going to bring a friend on our date. I got really freaked out and upset, so I canceled the whole thing and never met up with him.

Story #2: A few years ago I started talking to a guy online, and we wanted to meet up but had really tough schedules at the time. Since he worked near me, we decided to have a ‘train date’– I’d meet him at the T stop, and we would take the train together to my evening class destination. Sounds fun, right? I walked up to the T stop and met him, and instantly knew there was just no attraction (on my part). So great. Now I’m stuck with this guy for a 30 min train ride. Even worse, we were having this awkward train date with a hundred strangers all around, listening to our every word. I kept suggesting that he get off at the next T stop, but he liked me and didn’t want the date to end.

So we’re awkwardly standing together in Park Street Station when I feel a tap on my shoulder, and who should it be but one of my friends! Of course she wanted to know what I was doing and who my ‘friend’ was… Talk about bad timing.

6. The dress code violation.
I don’t have any one story for this, but it happens ALL. THE. TIME. Guys, can you at least TRY and put some effort into dressing up for a date? Maybe tuck in your shirt, or wear nice shoes? It doesn’t take much. The worst is when I dress up and the dude is super under-dressed– then I just end up feeling really stupid. And that doesn’t make for a good start to any date.

7. The declined credit card.
Thankfully this has never happened to me. But I have been in situations where the place only takes cash, and I only have a credit card… that’s not necessarily super awkward, unless I know that I’m never going to go out with this guy again and now I’ve basically forced him to pay for me. (My take on paying is– always offer to go halfsies on first dates. If the guy wants to pay for the whole thing, great. If not, fine too. If there is a second date, whoever asked the other person out should pay. And if there are dates beyond second, then we can trade off who pays).

8. The lack of conversation.
This is the second worst thing that can happen on a date. First worst, being no attraction.

Last year I went out on a date with a Harvard post-doc. First, he suggested that we meet up at an Au Bon Pain. Guys, that’s not a good date location, OK? Second, he was at least 30 min late, so I bought my own coffee. Third, the ABP was inhabited by freaks and homeless people. Fourth, when this dude finally showed up, we sat there and didn’t talk about ANYTHING. This is a guy who was in neuroscience and spent the previous summer giving TED talks on his work. I wrote the whole thing off as a terrible experience, but then he asked me out again!!!

Guys, if you’re interested in me, then ask me a freaking question! I can’t spend the whole date carrying the conversation and asking you questions ad nauseum. If I like you then yes, I want to know more about you. But I’d like to have an opportunity to also tell you a little bit about me, too.

I didn’t go out with Harvard dude again. And I’ve never gone back to that ABP.

1 Comments on “8 Awkward Dating Moments”

  1. Pingback: Don’t Date (Or Be) This Guy | Southern Girl in the City

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