82. March 2013: How to Turn a Good Date into a Bad One

How did you meet? Online

Name: James

Height: 6'2"

Age: 37

Occupation:  producer/screenplay writer/ probable misogynist 

Good quotes from date(s):

Him: Ugh, I can't believe you like those TV shows. They are so contrived."

Me: Isn't everything on TV contrived? What shows are you into?

Him: Breaking Bad and Mad Men are great. 

Me (in my head): You couldn't be more hipster-cliche. I feel like I'm in an episode of Portlandia

Why is he still single? Comments will explain

Did he pay for the date?  We split it

Did he contact you after the date? No, he learned

How many dates did you go on? 1

Would you recommend to a friend? No way


 In all my 81 dates I've NEVER had one that went from interesting to horrible so quickly like this one. It was going well until he said the following:

1. The hot girls he's dated from OkC

2. The hot girls he's slept with from OkC

3. The anorexic and chubby girls to he's met from OkC

4. Anorexic doesn't do it for him because he likes an ass he can grab

I could go on but you get the idea. He's really an open-minded guy - he tried to explain - because even though the women were super-hot (like in the 2% category of hot - a direct quote) they were boring. And he needs more substance. 

Maybe that's where I come in?

Towards the end of my second drink he went off on this diatribe about women's weight and how that relates to their ass size and I shut down. I have no desire to argue with someone so "open-minded". When he finally stopped talking, he stared at me and I felt uncomfortable. He asked what I was thinking and I said "Nothing". 

He decided to project his insecurities on me and tell me what I was actually thinking about him. I told him he was being aggressive and I didn't like it. I got up to leave and he followed. On the walk down the street he seemed to be remorseful about his douchy behavior, because he tried to make banal conversation about the weather and the neighborhood. 

I nodded my head and let him apologetically hug me before we parted ways. He knew he sabotaged the date and I only hoped that on his way he home he tried to figure out why. I assumed it was not the first time he turned a good date into a complete disaster. 

On my way home I felt sadness and disappointment, feelings I don't usually have about dating. But I felt tired and wanted to cry a little, not just for myself but for all of us. For all of us who get dressed up and put on makeup and have hope every time. 

Because we can bullshit each other and say we have no expectations about these dates, but one thing I always have is hope. Hope that this is my last stupid online date...for forever or even just for the next 6 months. I took my sadness and plunged it into eating some delicious chicken fingers afterwards, because my expectations of chicken fingers are always, always fulfilled. 

UPDATE: A few months later, here's what happened when I saw him again...

56. November 2011: Gary: "You're Dismissed"

How did you meet? online

Name: Gary

Height: 6'2" (I can't confirm this as he never stoop up. Remember in the olden days when men stood up when women entered and exited a room or got up from the table? That must have been lovely)

Age: 38

Occupation: digital something or other

Good quotes from date:

"Dating is so easy for super hot people." (Implying that neither one of us are in that group.)

"I need a new fuckin' job." (After we'd agreed to stop talking about work.)

"Don't be mean." (After I told him, in jest, to stop talking about how fabulous his new apartment is with 5 closets and a washer/dryer.)

"I had a shitty day. I'm going to stay for another drink. I get it, I got it. You can go." (After 60 minutes of torturous conversation.)

Why is he still single? I think his quotes above sum that up - and he's a young curmudgeon.

Did he pay for the date? yes, he was still running up his tab when I was dismissed

Did he contact you after the date? No, I'm sure he could tell that I didn't like him

How many dates did you go on? Barely 1

Would you recommend to a friend? NO.

When you're 38 looking for a long-term relationship and something "real" per your OkCupid profile because all your friends are married with kids, I would think that you would want to give every date a chance and put on your best game face. Gary, or "Debbie Downer" as I will refer to him, had a "shitty" day and clearly was not in the mood to get to know me. 

I may not be "super hot" or whatever the hell that means since that is something that 16 year-olds say but I'm pretty cute especially in the new silk shirt I was wearing. I too was tired and had a long day at work but I still brushed my teeth and hair, put on make-up and smiled when I greeted him. 

Debbie should of been an adult and canceled the date. Self-awareness is the key to living, my friend. Debbie didn't ask me any questions or say anything interesting at all.  Even when he was talking about his hobby that makes him "very happy" he did not crack a smile, he did not change his tone of voice like Eeyore from Winnie the Pooh.

During the awkward silences (and there were many) I talked to the friendly bartender and the men near us who we watched buy wine for two women they didn't know. "Don't worry you don't have to talk us.", they said to the women. I leaned over, "That was nice of you!" I exclaimed to one of the men. He replied with a smile, "Hey, life's too short." I couldn't agree more.

54. October 2011: Seth, The White Rapper

How did you meet? Hipster speed dating (like regular speed dating but at a shitty bar)  

Name: Seth 

Height: 6'0" 

Age: 28 

Occupation: markets some luxury product


Good quotes from date: I arrived at the bar a few minutes before him. He came up behind me and greeted me with a "Yo."* Nothing says romance like a two word greeting that only rappers and 12 year-olds use in a non-ironic way. 

Sometime during the date: "I usually don't date white people" ** (File under WTF)

The end of the date: "I'm gonna bounce." *** 

*He is a WHITE person - a half jewish guy from the midwest!
**I'm a WHITE person.
**Nope, he's still WHITE. And still not a rapper. 

Why is he still single?  See EVERYTHING I've written. 

Did he pay for the date? When the check came I found him so offensive that I actually wanted to pay for my own drink so I wouldn't have blood on my hands. I threw down a 20 immediately and told him I'd get change to give him. He told me he'd pay. I asked why (me being a WHITE person and all...) and he said, it's because you work in non-profit. Hahaha, he giggled. What a peach.

Did he contact you after the date? Oh god no. 

How many dates did you go on? 1 

Would you recommend to a friend? only to my non-white friends...JK. NO 



Ladies and gents I'm going to confess that I was really excited (and even a bit nervous) for this date, which is a rare feeling these days. I had high hopes mostly because we'd already met and I knew he was cute and funny and an excellent dresser. 

And since we'd already met he knew I was a WHITE person. The sad part about that comment is that just before, he was telling me why he went to speed dating...because he feels really ready for a serious relationship. He's been single for over two years and is tired of casually dating.

I don't see how I could NOT be offended by that comment. It's like going on a date with a brunette and saying, "Well I'm really into blondes, they're hot." Except you can actually change your hair color but I'll continue to be white no matter what. 


I'll confess that after that I didn't find his weird, immature, hip-hop speak cute or charming anymore. I became a snarky passive-aggressive bitch and just wanted to go the fuck home.  I don't like people that waste my time and think it's funny. 

He for some reason walked me north a couple of streets with his bike and then hugged me awkwardly with the bike between us (symbolic no?). He then said, "We'll hang out again." Like a statement. Like I was waiting for him to say that. Like he thought I was into him and wanted to see him again. 

As I trudged home in my sexy heeled boots (I wore heels for this guy!) thoroughly disappointed I remembered that I once dated a guy exactly like Seth when I was 26. His name was Wayne and he too was cute, smirky, semi-charming, a good dresser, and he also said immature, offensive shit that at the time I thought was hilarious. He was too cool for school and when my friends met him they thought he was a huge asshole. 



They were right of course, but I made some excuses like "when we're alone he's a different person." Blah, blah. We dated for 3 months before I had a come-to-jesus-moment and agreed with my friends. 




I'm happy to say that 6 years later, thankfully, I can smell this type of dude right away and I have learned to run as fast as possible (in heeled boots).