Once upon a time…

While I was living in Chicago, a co-worker of mine discovered that I was newly single and came up with a grand idea:

“I’ll hook you up with my girlfriend’s gay best friend! You’d be perfect together!”


—YEAH. Find one gay man who hasn’t heard that line from a hetero with good intentions before.

Having just gone through a break-up AND being in the midst of “cuffing season” in a new city, I agreed to meet the boy for a date.

I’ll admit that when my Uber driver dropped me off at a hipster’s wet dream of a diner in Wicker Park, I had high hopes. I was so relieved when I walked in and a cute latin boy with an immaculately sculpted “hipster hair cut” waved me over to his table. While his lack of facial hair and being slightly tubbier than he appeared on SnapChat wasn’t ideal, I had no energy to be picky.


After a couple hours of amazing conversation, per his idea, we went to a local shop and bought a couple bottles of wine and dessert. We took our groceries to his apartment and started watching a movie. We only planned to hang out for a few hours since he’d informed me of his plans to catch the train into the suburbs that evening. After a little 3rd base action & an accidental drunken nap, we Ubered to the train station and reluctantly said our good byes.

Suddenly, just like a classic Carrie Bradshaw moment in Sex and the City, as I waited on my train platform he called me:

“I cancelled my trip to the burbs; I want to spend more time with you.”


Being the hopeless romantic that I am, these magic words gave me butterflies. He picked me up from the train station, we grabbed dinner and more wine and went back to his place.

After just a few minutes of cuddling on his couch he looked down at his blinking phone and his face turned bright red. He lifted my legs off his and said:

“Um…So I think my boyfriend might be showing up.”


I replied, “EXCUSE ME?! What boyfriend?”

Before he could utter a response, sure enough, the front door unlocked and a guy walked into the apartment. He said “hello”, and I said “hello” back as I scrambled to request an Uber and get out of dodge. The guy immediately disappeared into the bedroom. I had no idea what to do for the 9 minutes my app told me it would take for my driver to arrive. In a feeble attempt at damage control, I said loudly:

“I can’t wait to double date with you guys. My BOYFRIEND can’t wait to meet you!”

Mortified, I immediately walked outside. As I waited for my driver, shivering cold on the trendy street corner of his vintage neighborhood, I received a text:

“I’m so sorry about this. I was having such a good time with you that I didn’t want to ruin the mood by telling you I had a boyfriend.”

I never replied.

I spent the 25-minute cab ride drunk-venting to a sweet, elderly Russian driver about how much I hated men & Chicago.


When I arrived at work the next day I was greeted by apologies from my co-worker. But I just laughed and told him not to worry and that it wasn’t his fault. While I was initially disappointed and freaked out by this experience, I knew that it’s retell value would make it worthwhile.


Was there a lesson to be learned from this disaster date? Yes actually. I learned that people are capable of omitting ENORMOUS details, ie: a boyfriend who has keys to the apartment I’m dryhumping them in. After this date I began to ask more questions. Waiting for people to volunteer information, no matter how minute or monstrous it might be is a terrible idea. Like the old saying goes, “You live and you learn, and then you never go on blind dates set up by straight co workers again.” #LessonLearned

Posted by:Anthony Black

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