Stupid little Cupid

Does Valentine’s Day make you feel insecure? Are you jealous of your friends and family members who have “perfect” relationships, and wondering why you and your significant other can’t live in that same paradise? Too often, it seems as if the grass is greener on the other side of the fence, but sometimes all it takes is a little closer inspection to see that the grass hasn’t fared so well over there.

Bad dates.

Bad dates.

I asked some readers to share their “brown grass” stories, and tell me about the times when Cupid’s arrow missed its mark. Some of them were all too happy to describe the dating disasters and relationship wrecks they’ve survived, fortunate enough to learn and love again.

So next time you’re wondering if you could do better, remember these anecdotes, and think about what’s out there. Then think about what you have. So what if he watches a little too much football? Who cares if she snorts when she laughs? At least they don’t go to higher levels of awkward, shocking, or downright crazy, like some of these folks did….

Going so low

The dating disaster that sticks out the most in my mind was when my date for the prom took me home early, so he could go back to the prom by himself.

At least he was honest

One of my girlfriends asked me to try speed dating with her. One guy I met had some trouble with English, but I got his message loud and clear. He kept stating, “Want to marry woman, and make babies” over and over again. Needless to say, I was not hooked.

Hope he wasn’t too incensed about the issue

I was on a first date as a 20-year-old college student with a slightly older guy. After dinner, where we had been at a comfortable distance from each other (across the table), we were out on the deck of the restaurant looking out at the view. I caught a whiff of something that to me seemed rather pungent and nauseating. I looked at him quizzically and asked, “Do you smell bug spray?” He said he didn’t smell anything.

The conversation continued, and the smell only grew stronger. Finally I asked again if he smelled it (I described it alternately as bug spray or “something really toxic”). Finally he leaned forward to expose his neck and asked me to see if it was his cologne. This was my first experience with patchouli!

Apparently I had scored myself a first date with a reforming hippie who was holding onto the last vestiges of counterculture – in a very big, very smelly way! I realized I had inadvertently insulted him, and the remainder of the date offered no opportunity to recover (for me or for him) so needless to say, it was both a first and a last date.

Brett, if you’re still out there, I’d like to apologize and introduce you to my little friend, Gucci by Gucci.

Fool me twice, you’re insane

I was new to Raleigh, and didn’t know a soul other than the people at my office. An old friend came to visit, and invited a friend of his to come over for a party I was throwing – she lived in the area and was equally lacking of a social life. We had fun together, so I later asked her out. The date went well, and I said I’d call her the following week. Apparently, that wasn’t soon enough, because the next morning, I was awakened by her knocking on my apartment door.

She’d shown up without calling first, with the makings of a full steak dinner and a bunch of board games. A blizzard was closing in, and she apparently wanted to get snowed in with me – after one date. She grilled up the steak and opened a bottle of wine. She ate a salad, since she was a vegetarian. It was still early in the day, so I didn’t want to drink wine, but she had some. I kept dropping hints that she shouldn’t have too much, because she’d need to drive home before the snow started falling, but she ignored me. She spent the night on my couch, and the next morning I told her I had to go to the office, just to get her to leave.

I foolishly asked her out again, but we had an honest discussion about boundaries and surprise visits. She told me she wouldn’t dream of dropping in with steak and wine again. Apparently, she drew a fine line between “dropping in” and “dropping by” because a couple nights later, I walked outside to find a card from her, taped to my door. The card’s printed message was cute, but her handwritten note inside was not – she was angrily telling me off for not having called her for two days. (It’s important to note that we hadn’t committed to anything long-term, and I hadn’t called her that frequently prior to this.)

So, after I’d asked her not to come over unannounced to make me lunch, she came over unannounced to leave me hate mail. I broke up with her by phone, then spent the next few weeks avoiding my apartment as much as possible, keeping the blinds down when I was there, and feeling thankful that she didn’t know where I worked.

Next time, ask about the Primaries

I wanted to talk about our slow-moving relationship, and was really looking forward to getting “the conversation” out of the way. We went to a nice restaurant and we were chatting for a while about our weeks, etc. when there was a break in the conversation. I jumped in.

(This is all paraphrased since my recording device was on the blink.)

Me: “I have a question for you. It’s about us.”

Him [looking a bit nervous]: “Okay.”

Me: “The pace of this relationship… How does it seem to you?”

Him: “Slow. It seems slow. Though I’m not sure what determines the pace. How does it seem to you?”

Me: “It seems slow, and I’m not sure what determines it in general, but in this case, I think it’s you.”

Him: “Well, I have a bad habit. If I think something has a lot of potential, I over-think everything and in this case, I was afraid to rush things so I guess I’m doing the opposite. I’ve had bad experiences in the past with rushing things.”

Me: “Okay, that makes sense. It just seems like we keep having our second date over and over again. I think it’s strange that we’ve gone out as many times as we have and we’ve never even made out. I’ll admit that I don’t know what you’re looking for. Are you looking for a long-term relationship?”

Him: “Yes, I am. And if you had asked me two months ago what I was looking for in a woman, my answer would have described you.”

(Now I was thinking, “He’s head-over-heels and scared… I didn’t expect this and I can’t say that I feel the same way.”)

At this point, he rambled a little bit about these past experiences, blah, blah, blah. And then he thanked me for bringing this all up because he totally agrees with me that it’s moving slowly. We were at a restaurant near his house, so at this point, I’m thinking, Okay, I guess we’ll go home and finally make out. I’m not exactly sure if I’m looking forward to it.

We talked about a few other things, and I started feeling really good about the conversation. Then I said, “I have one more question for you.”

Him: “Yes, the answer is yes.”

Me: “It’s not a yes-or-no question… What are you answering ‘Yes’ to?”

Him: “I’ll just let you ask what you were going to ask.”

Me: “No, really, I need to know what you’re answering.”

Him: “You were going to ask if I voted for George Bush.”

I’m no longer seeing him.

He can’t take her anywhere – especially to a Fancy Feast

So I am out on a second date with this older, rather prominent attorney. We are at an annual party that one of my neighbors throws. Huge deal – Elizabeth goes all out with the food, most of which she prepares herself, and has strategically placed hors d’oeuvres around the inside and outside of the house. It’s getting dark and they have hired a Mariachi band to come down the street, down their driveway and up the deck to perform for 20 minutes or so. My date and I are sitting on the brick partition going down the driveway and I take a handful of a snack mix sitting beside me. Well, it is awful, and literally starts to expand in my mouth. I’m trying to pretend that everything is okay, but my date looks at me and realizes that I am about to throw up so he hands me a handkerchief (yes, that’s how old he is) and I spit it into the hankie. About that time a girl that I have only met once or twice comes over and says, “Hey, _______, I hope you remember me. Did you just eat cat food?”

Is it because his bouncer made you feel uncomfortable?

I decided to do some online dating, and had talked to this guy on the phone a few times. He seemed really nice, and we had matched interests. He had been an attorney before moving to Portland, and now was a pig farmer (not my usual draw). I was trying to stay open-minded.

One day he called mid-afternoon and asked if I wanted to go for a drive. Since I had only met him in person once at the street market, I passed, because it was still too early. He mentioned he needed to drive around Portland for some money pick-ups. He then confessed he had another job in Portland that he’d hesitated to tell me about, since it seemed to be a deal-breaker to a lot of women.

He owned about 20 adult entertainer dancing locations across northern Oregon – the ones that are little houses with the “peek-a-boo” style of watching. He said he used to date the dancers but he doesn’t anymore, and doesn’t like to mix business with pleasure, but his girlfriends had trouble with the drama and late night calls of the dancers.

That was the last bit of conversation we had.

“Your what?”

Some friends of mine had set me up on a date with a really nice guy. He picked me up and we went downtown for some dinner. It was really fun, but a little bit after dinner he casually brought up that he and his girlfriend had not been doing very well. I ended up excusing myself to the restroom, and texting one of my girlfriends, “he has a girlfriend!”  When I returned I told him I was ready to go, and when he dropped me off, he asked if there was anything wrong. I simply mentioned I don’t date guys with girlfriends, and he should take care.


I met a woman at a Raleigh meetup. After a few weeks we became intimate, and she was curious to know if I’m dating anyone else. I said, “No; what about you?”  She said, “Except for my husband, no.”

I thought we were pretty close and exclusive, so I giggled a little at this thought – I’m not married, but my girlfriend is….

I like her a lot, so we remain friends.

No introductions necessary

In high school, I had been interested in this girl (we’ll call her L) for a while, but lost interest after some time. That was about the time she became interested in me, apparently, so she asked me out. I agreed, figuring maybe I would be able to rekindle my interest in her.

She told her best friend (we’ll call her A) about it, suggesting she invite along her boyfriend and we make it a double date (an element of which I was unaware). We had a hard time agreeing on what movie to go see, and finally settled on The Polar Express, with her strong interest to go see it and my fairly mild apathy.

I showed up at the theater, having been dropped off by my sister, to see L and A there, along with A’s boyfriend. And A’s brother. And A’s parents. Seems that A had completely misunderstood what was going on, and had invited her whole family along, not realizing L and I were on a date.

Pretty awkward already, but it gets worse: I was able to quickly identify A’s brother and parents because A is an ex-girlfriend of mine.

Try to keep your stories straight

My cousin was on a group dinner date with five couples – some married, some not. The topic of “Do people actually consummate on the wedding night?” comes up. Stories, laughter, drinking. One guy starts telling about him and his wife in the back of the limo on their wedding night, all over each other. You can tell his wife’s not happy this is coming out. He keeps going. She’s stone-faced. He finishes, red-cheeked and laughing, then looks at her. The table is quiet. She says, “That must have been your first wife.”

People didn’t even wait for the check. The moral? Get married…once.

No wonder he ordered the foot-long

I called a guy I’d met in a bar, and we had a brief but pleasant conversation, setting up a date for the weekend – the ever-safe dinner and drinks. Somewhere around when the appetizer arrived and I was halfway through my first drink, Joey hit me with an unusual bit of flattery: “You’ve got really nice feet.”  I stopped chewing and glanced down under the table at my French-manicured, sandal-clad toes. “They’re almost perfect – the way your toes go in order like steps.”

I laughed a little (albeit uncomfortably) and acknowledged this strange compliment with a “Thanks.” Then he asked, “Do you ever paint them red or pink?”

“What? My toes?” I said, taken aback. I couldn’t believe we were still talking about my feet! “Yeah,” he said, “I mean, I like the French manicure and everything, but I really like pinks and reds on toes best. French manicures are really more for hands.”

I had no idea how to respond, so I took another healthy sip from my drink, and said, “Well, yeah… sometimes I paint them red, but I’m not really a pink kind of girl.” I was pretty confused… I couldn’t figure out what the heck was up with this guy, so I tried to change the subject.

He later brought it back up by asking, out of the blue, if I enjoy foot massages. I said sure, from my pedicurist, but other than that, I really don’t indulge in them. His response: “I’d love to give you a foot massage.”

By this point, the waiter had finally arrived with my second drink and the entrée. I promptly began digging in just to avoid any more feet talk, when Joey said, “Well, would you like that?”

I said, “I’m sorry… what?” He said, “If I gave you a foot massage… would you like that?” Another healthy swallow from the martini glass, and I leaned across the table conspiratorially and said, “You do know it sounds like you have a foot fetish, right?”  And he said, like it was the most perfectly normal thing to be discussing on a first date, “Yes.”

Shocked, I think I finished half my drink. He then proceeded to tell me that he probably wasn’t the first foot fetishist I’d met. In fact, he felt quite sure that at least one of my previous boyfriends must have had a foot fetish. I’m not really sure why I bothered, but I argued this point with him, explaining that I had never had any boyfriend who willing offered himself up as my foot masseuse. He said, “How about one who liked licking your toes? Or sucking them?”

I said, “Eww… no!” He said, “Well, if not a boyfriend, what about a male relative?” I almost choked on my food then, and washed it down with the rest of my drink.

To top this fine evening off, he offered to suck and lick my toes that very evening if I was willing. The only thing I was willing to do at that point was flag down the waiter and ask him to bring the check as quickly as possible.

What, you don’t like having him write poetry about you?

First, there was the guy whose dinner conversation consisted of asking if I fart when I do yoga and if any of my ex-boyfriends were “hung.” Then there was the dude with a chronic ear condition who took us to a hibachi grill, held his hands over his ears the entire time, and said he’d commit suicide if his ears continued to bother him. And of course, there was the boy who wiped snot all over his hand just before serving himself from the pizza we ordered to share. And here I thought anchovies were my least favorite topping!

Honestly though, I think this last story is my absolute favorite. I’d had a lovely date with a guy who runs in similar art circles, so when he mentioned he could use a new harmonica, I gave him one that I had since I never use it. Through the wonders of Facebook, I found out that less than two hours later, he’d driven to his ex-girlfriend’s house and given her my harmonica as “a present.”

But that’s really not the best part – it’s what came after that. He was so mortified that he’d been caught that he left an old ratty guitar on my front porch “in repayment” along with a note that said I am fresh air during the pollen season and a great person to be stuck beside in traffic during the red light of his life.

After that last guy, I swore off dating, indefinitely. Then, the very next weekend… I met my future husband.

Now, after reading about their love lives, don’t you feel better about yours? Happy Valentine’s Day!

[Portions originally published in the January/February issue of Midtown.]

About Dan Bain

Dan is an award-winning humorist, features writer, emcee and entertainer from Raleigh, NC. His collection of humor essays, A Nay for Effort, has earned him fans from one end of his couch to the other. Why not join them and buy one? (You won't have to sit on his couch.) Dan will donate 10 percent of the book's proceeds to education. You can check it out at; thanks!
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2 Responses to Stupid little Cupid

  1. Oh, some of these sound treacherous! I think my funniest date was in high school. I dated a really serious, competitive guy- He took me bowling one night. We both were horrible bowlers. But, somehow, I managed to cream him. He was so angry and frustrated, he took me straight home and couldn’t even bring himself to give me a kiss goodnight. ha!

  2. After all that (and two failed marriages), I’m perfectly happy to be single!

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