Top 5 Worst Dates of All Time

You know you’ve had them.  We all have.  A person you meet has a lot in common with you; you seem to get along well, for some reason or another you think they may be date-able.  Either you or they take the plunge and ask “you want to go…” and next thing you know you’re shaving on a day you wouldn’t normally shave and rolling on an extra dab of deodorant for just a little extra protection for the big night – the big night of disappointment.  Be it an awkward conversation, a comment that ended up being rude, bad service, or a tragic series of events gone afoul, the fact remains that we’ve all been on them:  bad dates.

It doesn’t always have to be a first date, sometimes you are well on your way to coupledom – it even could be with a (current or future) spouse (you will note, #3 was a date with my husband).  Here are my top five worst:

#5 Let’s Not Beat Around The Bush, Here…

My least horrible date of all time was with a guy that I had hung around with a little while in community college.  We were in a few classes together and long story short, friends led to him asking me out one day towards the end of my last semester in community college.  On the evening of that terribly tragic night out, though, he picked me up and drove me straight to the town make-out spot and said “let’s not beat around the bush, here … I want you, you want me …” Twenty minutes later I was at home, still hungry because I had thought we were going out for dinner.

#4 The Night I Was Promoted To Therapist

And then there was that one guy that I also met at community college, a little bit before #5.  This one was slightly worse only because I had gone out with him once or twice before the worst date occurred.  I had started actually liking him, and we had a fun time.  And then we went to the harbor for smoothies and to watch the boats one day and he ended up unloading all of life’s problems on me.  His childhood was awful, his family was dysfunctional – an hour and a half later, I learned he had been diagnosed bi-polar and obsessive compulsive.  I felt like I should charge him an hourly fee for my time.

#3 Macaroni and Cheese Gone Bad

My poor husband, being made an example.  This date is more humorous than bad, but it nonetheless makes it on the list.  When we had first started dating, my husband and I had a conversation about variations to making macaroni and cheese, which turned into a “well let’s make some and hang out and watch movies!”  On the blessed evening, we watched Blue Velvet and made macaroni with barbeque sauce in it, and (again, my poor husband) thought he would wax eloquent and suggest we drink some wine with our mac and movie.  As I learned that night, though, he doesn’t have much of a tolerance for alcohol, and so three or four glasses in he was pretty tipsy.  This wouldn’t have even been an issue if only he hadn’t gone in to describing for me an article he recently read about women and arousal.  Another thing I learned about my husband that night is that when he drinks he talks louder, and louder, and louder until he is yelling in your face.

#2 We’ve Got A Bleeder!

A real doosie, number two was with a guy I also met (surprise! surprise!) at community college, immediately after I moved to California.  When I first came I knew very few people, so was pretty amenable to just about anything.  Even going out with a guy that had no car to drive me in, who had planned a romantic evening of playing video games in the family room of his parent’s home.  As this winner of an evening came to a close, I was walking outside to my car and – despite all of my cues that a goodnight kiss was not going to be given – he forced one on me anyway, biting down on my lips so hard that I bled the entire way home.  The next day in class, he was referring to me as his girlfriend and then broke up with me three days after that when he saw me flirting with another guy.

#1 What Women Want

The #1, all time worst date I have ever been on wasn’t even supposed to be a date.  A guy I met at my first California job asked me to see the new (at the time) Mel Gibson flick, What Women Want and while I said I wasn’t ready to date (having just broken up with my boyfriend), I was still willing to hang out with the guy.  When I showed up at the movie theater (we met because, as it turned out, he didn’t have a car either, and was trying to conceal that from me), he clearly had made it a date despite my protests.  A part of the way through the film – I think around when Gibson does that horrible pantyhose in the bathroom number – he asked if I would be offended if he put his arm around me.  I can still remember, vividly, myself replying “look, I am not ready for dating and I really would be offended.”  And yet, he put it around me anyway.  This was not what made it the worst, though.  No, no, no, fine blog followers – this date had not even gotten to its worst point yet.  A few minutes after putting his arm around me, Don Juan who wouldn’t take “no” for an answer began scratching himself, which he proceeded in doing for the remainder of the film.  I thought he must have something wrong with him, so never hung out with him again.  Of course years later, many of my male friends informed me that he wasn’t actually scratching.

So there you have it, my Top 5 Worst Dates of All Time.  Lessons learned?  Apparently dating guys you meet at community college is not a good idea.  And bring a credit machine so you can charge an hourly rate for therapy if things end up going that way.  Being married, Date Nights that go awry fortunately can be remedied by going home and heading to our separate corners of the household.

What are your five worst dates?


  1. Auntie Mary

    My dear niece — you are a lightweight if these were your worst! But I enjoy your writing style; I started a book meant to be a comedy on my single adventures, but it started sounding so pathetic and sad, I bailed on it; I only amuse myself it seems! Keep up the good work; I am glad you found a keeper in your cute husband!

  2. Heather Christena Schmidt

    Haha – thanks Jake! I felt awkward for me too!

  3. Jacob Silver

    I feel awkward for you.

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