10WorstMovieDatesWe’ve all been there—the horrible first date we knew we should have left after the first five minutes.

One of the most absurd dates I’ve ever had was, if I’m really honest about it, my fault. It was my fault because, though I’m not responsible for the gentleman’s actions, I ignored a feeling in the pit of my stomach that said, “End it now.” Thirty minutes into the date, I knew this was not the guy for me, yet I allowed the date to go on for another three ridiculous hours because I didn’t want to seem rude, reactionary, or like a bitch.

I met Mr. ___  at a fundraiser gala for a charity. I felt and looked great and he looked great and we were drawn to each other immediately. He was good-looking and charming and funny.  We lived in different cities, but I had an upcoming business trip to Chicago, where he lives, and I couldn’t wait to go out with him.

He had planned a nice evening for us; one that would allow me to have a fun experience in one of my favorite cities. I didn’t know the plan ahead of time, but I didn’t really care, because I love Chicago and assumed I’d enjoy whatever was on the agenda. We started with drinks at the new restaurant in the lobby of my hotel.  As we were waiting for our drinks, he began to brag about his sexual prowess with more detail than I cared to know (which was none). I made a rather lighthearted comment about this not really being first-date conversation.  He accused me of being uptight. 

And he continued. This guy was in his 40s, but I felt as if I were with a 14-year-old who was just discovering sex.  It was so sophomoric. This would have been a good time to thank him for the drinks and excuse myself.  But I didn’t.  As a single woman in my 40s, I had often been accused of being “too picky.”  Not wanting to prove that notion to be right, I stayed, even while Mr. ___ disrespectfully continued a conversation I had made clear I didn’t want to have. I stayed, waiting for the charming gentleman I initially met to show up. Where was that guy?

Next on the agenda was dinner, then a visit to a show at a club he belongs to. I convinced him that I wasn’t very hungry so we should just grab something at the club.  I didn’t want to spend more time with him than necessary, but also thought a show would be fun.  Yet I was still pushing down that feeling in my gut that’s saying “I should just cut my losses and head back to my room.”  There was something odd and aggressive and just not right about this guy.  But off to the club I went.

We got to the club and I was immediately confused.  All the staff knew him, and so did all the performers.  But we were at a private club and the performers were all drag queens. I wondered how often he came here? Drag shows can be entertaining and a lot of fun, but I don’t know that this is something that many straight guys do on a regular basis. But I said nothing, because I was still trying to be a good, open-minded, non-uptight date.  But now I knew something wasn’t right. 

Finally I asked him what made him join such a club.  In a very nasty tone, he explained to me that he “loves everybody and doesn’t judge anyone.”  This exchange was so unpleasant that it was another opportunity for me to leave.  But I didn’t. I told myself that I should be patient with him.

During the course of the first show (yes, he wanted to stay for two), I made a comment about some of the performers not being very good.  He very angrily explained to me how brave they are, how hard their lives are and how rejected they are by society (none of which had anything to do with not being very talented).  His reaction was so strong that it was at that moment that I realized what his problem was: The over-the-top, graphic sex talk, the membership at this club, and the anger at any mention of the performers all said to me that he was, perhaps, struggling with his sexuality.

And that was fine.  He needed to work that out.  What I needed to work out was, Why did I ignore my gut feeling hours earlier, when it was clear that this was not going to be an evening I would enjoy?

After the second show, he dropped me off at my hotel and said, “Is 8:30 still okay?” Geez, I’d forgotten that, early in the evening, I had agreed to breakfast the next day.  I should have said something like “It was nice seeing you, but I think I’ll pass on breakfast.”  What I said was “Okay,” and I’m still not sure why.  I think I was feeling sorry for him; if my theory about his struggle with who he really was was correct, than I had started to see him as fragile, and I wanted to be a “nice girl” and not reject him . . . even though I had no desire to see him and his vacillating moods again.

Breakfast was awkward as we made small talk about nothing, including no mention of anything we saw or did the night before.  I paid the bill, which he didn’t appreciate.  He called me out with, “Women like to pay the bill when they don’t want to feel like they owe you anything.”  He was right.  He’d paid for everything the night before and, even though I knew I didn’t owe him anything, I just wanted to dispel the notion that I would let him pay for everything and would ditch him anyway. 

This time, when he dropped me off at my hotel, I just said “Thank you.”  We never spoke again.

I shared this story with a number of single girlfriends and we all acknowledged that we have stayed too long on dates we didn’t want to be on just so we wouldn’t be seen as too picky, difficult, and whatever other hostile descriptions single women are sometimes labeled. 

I so much wanted not to be called a user, high-maintenance, a bitch, that I ignored my own feelings in the effort to protect his.

I’m over it, though. That was the last time I did that. There’s no reason to tamp down my own feelings and give away my power just to make my date feel better.

My book, The Spinsterlicious Life, has 20 life lessons for being happily single.  This should have been Lesson 21: Always trust your gut, and be brave enough to act on it.


RELATED: My Worst Date Ever: One Woman’s Nomination – Anonymous



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  • Kaypee December 9, 2014 at 8:23 pm

    Thanks for sharing this. I agree with you. We should not ignore our feelings just to please others. The lesson that I learned is that, the moment I realized that a date is not what it supposed to be, leave. Why waste a couple of hours or even minutes? After all, the probability of you two seeing each other again is very thin. So do not be guilty for leaving your date behind.

  • ellensuespicer-jacobson June 7, 2013 at 9:56 pm

    Your gut never lies! Your body has a mind of its own, separate from the brain, so listening to your gut maybe smarter than using your brain to rationalize. But you learned a valuable lesson, so the date was not a total loss. Just another frog to leap over!

  • Jennifer Cheyne June 6, 2013 at 12:41 am

    Woops, apparently I’d do well to spend all the time I’ve gained not going on bad dates proofreading my own posts!

  • Jennifer Cheyne June 6, 2013 at 12:39 am

    Oh my god, that was terrific. I have been that woman too often in my life – thank heavens, not anymore. I used to have a hard time even saying not when someone asked me a date, when I was very young. I remember in one case, when the guy called to set up the logistics of this date I’d agreed to, I said, “Actually, my parents are very religious and they don’t want me to date anyone outside our religion. Sorry – I guess I forgot.” Lord.

  • Eleanore Wells June 5, 2013 at 6:28 pm

    @ Toni Myers: Thanks! I want you to read my book, too! 🙂

  • Toni Myers June 4, 2013 at 9:26 pm

    I loved your slightly scary tale, worried how bad it might get, and was relieved when it ended. I want to read your book!
    Thanks, Toni

  • Diane Dettmann June 4, 2013 at 9:30 am

    Thanks for the interesting and eye-opening date story, Eleanore. Reminds me of some of the dates I had when I was in my 50s after my husband passed away. After offering to pay my share of the dinner which was usually waved off with the “no, no, I’ll get it,” I couldn’t wait to get back in my car and go home! Author of Twenty-Eight Snow Angels http://www.amazon.com/Twenty-Eight-Snow-Angels-Widows-Renewal/dp/1432777041