Dating Matches from Hell

Editor@ESME
ESME.com, A Community for Solo Moms
6 min readSep 19, 2016

My adventures dating avoidants, narcissists, and an S&M aficionado

It was going well for a first date. He was tall and good-looking. He was wearing a tie. He paid for our dinner at a hip new place in town. He had good manners . . . was smart and funny . . . and he could kiss. Out in the parking lot next to my car, we were doing some serious smooching when suddenly he pulled my hair. “Stop!” I yelled. “You’re sure you want me to stop?” he asked as he pulled it even harder. “Yes, stop!” I repeated, and moved away.

“You’re not going to hurt me, are you?” I asked, thinking of my two children. “No, but we’re not going to have a second date,” he said with obvious annoyance.

No, we most definitely were not going to have a second date. I’m not passing judgment on consenting adults who are into hairpulling and other kinky acts, but isn’t there some kind of etiquette for determining if your partner is cut from the same cloth? The hairpuller had contacted me on Match.com with a very respectful e-mail, followed by a few days of texting in which we discussed the importance of good grammar, being single parents, getting our kids to clean their rooms, and the futility of lying on dating profiles. He also mentioned that sexually aggressive women freaked him out. (Hmm . . . that would have been a good time for him to inquire about how I felt about having my hair pulled.)

It was an awkward end to a date, to say the least. He never apologized or asked if he had hurt me, but said that his intuition was usually accurate and he had had a “feeling” about me. What, I wondered, could I possibly have said to this man to lead him to believe that I wanted the hair pulled out of my head while being kissed?

I drove home, crying all the way while contemplating wearing a hairnet on all future dates.

Just when did dating become a game of Russian roulette? I entered the dating market about three years ago — after my upstanding, corporate husband of 20 years ran off with his mistress — hoping to find a terrific man who was ready to embark on the next great chapter of our lives. At this point, I simply want to find a nice, normal man to go to a movie with, maybe someone who can reach things from the top shelves in my kitchen on occasion.

My Romeos to date include an emergency-room nurse who was 42 years old and ridiculously handsome. We met for the first time over Diet Cokes in the park at the hospital where he worked, and our chemistry was off the charts. This was my first rodeo after my husband left me, so it was enough that a man — any man — could find me desirable. We made plans to meet later that night, and I drove home with a huge smile on my face, conveniently ignoring the fact that this gorgeous specimen of a man and I were ludicrously mismatched intellectually.

When we met again, the first words out of his mouth were, “You won’t believe what my crazy ex-wife did today. . . . ” In fact, pretty much every conversation we had began with a harrowing story about his “crazy ex-wife.” (Crazy ex-wives have been a theme on every date I’ve ever been on. Not once has a man told me that his ex is a wonderful woman and that they simply fell out of love.)

The next day, I was walking through town with my 11-year-old son, and up popped a picture of Naughty Nurse’s member on my iPhone. “I can’t wait to kiss you all over,” said the accompanying text. I quickly deleted it, while simultaneously looking to see if anyone could tell that my chaste little phone had just become porn central. I quickly replied, “You can’t send me things like that!” and reminded him that my son could have been holding my phone.

Did I mention that Naughty Nurse has two young sons of his own and is a Boy Scout leader?

Next came the 51-year-old financial consultant who seemed to be my perfect match. After a delightful week texting and talking on the phone, I found him intelligent, funny, sensitive, and exceedingly polite. We were traveling merrily down Courtship Road until he took a detour to Crazy Town and began to text me obscene meanderings about the number of times we might climax during sex. When I reminded him that we hadn’t yet met and I didn’t care for sexting, he grew hostile and bombarded me with fanatical e-mails and texts about how I probably wouldn’t like sex enough for him; and, at one point, he warned that if his sister knew I had hurt him, she would kill me.

When I told my stalker not to contact me again, he filled my inbox with reams of e-mails apologizing for his “misjudgment” and “momentary lapse” and bemoaning the fact that he had found the perfect woman and had blown it. He sent flowers, he texted, he e-mailed. I remained silent until he finally gave up — perhaps he met another victim on Match.

After recovering from that trauma, I ventured out with a doctor in his 40s who arrived at our first meeting directly from a workout, dripping with sweat and in shorts. He ordered lunch before I got to the restaurant and proceeded to eat while I sat with an empty plate. My manners prevented me from walking out within the first 10 minutes, and he interpreted this to mean that the date was a huge success, texting me afterwards about getting together later that night. I declined. My standards are not unreasonable, but personal hygiene and pants are definitely at the top of the list.

I don’t remember dating being this difficult or physically painful. Apparently in the years I was out of the dating market men completely lost their minds. Looking back on the past couple of years, one fact is apparent: I have wasted a colossal amount of time on worthless men. If only Match.com were more like Facebook with a “Reviews” section, then women could post helpful hints for one another on the men’s pages.

Unfortunately, it’s every woman for herself. I’ve hidden my profile on Match. But deep down I know that, as much as I would like to swear off men for eternity, eventually the pain and rancor of my experiences will fade and I’ll jump back into that virtual pool again. Hope springs eternal, after all. When that day comes, I’ll be ready with my new profile:

I am a smart, funny, sarcastic, secure, vivacious 50-year-old writer looking to meet a man with whom I can spend the rest of my life. Intelligence, humor, chivalry, manners, wit, and a keen familiarity with grammar and punctuation are basic requirements. It doesn’t hurt if you are handsome and keep in shape, have a clean car and old-fashioned values that prevent you from ever considering going Dutch on a first date.

I like to cook, read, drink wine, talk on the phone with my friends, travel to exotic lands, and watch movies in theaters. I like dogs but detest cats. I prefer the country to the city, unless I’m shopping for shoes.

Please read all the way to the bottom of my profile before even thinking about contacting me.

If you enjoy taking selfies of your nether regions, don’t contact me.

If you are not on speaking terms with your ex-wife or girlfriend, don’t contact me.

If you don’t know the difference between their, they’re, and there, don’t contact me.

If you have any restraining orders against you, don’t contact me.

If you cannot bother showering and putting on a pair of pants for a date, don’t contact me.

If your idea of the perfect evening involves dungeons and black leather, don’t contact me. In fact, please get off Match.com immediately and sign up for Kinkdating.com.

If none of the above applies to you, please feel free to send me an e-mail. Be sure to include your home address, social security number, and a list of ex-wives and girlfriends who may be contacted for references. Once you have been vetted, I will reply to your e-mail with a psychological survey that will be reviewed by my therapist. The process takes four to six weeks, so please be patient!

Ah, dating . . . isn’t it romantic?

This piece was originally published at ESME.com

Written by Jaimie Seaton

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Editor@ESME
ESME.com, A Community for Solo Moms

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