Bad dates. We’ve all had them. They make great stories, but in the moment, boy, do they suck!

Being on a date is a lot like being center stage of an improv scene. No matter how much you plan, you have to work with everything around you. Show enthusiasm, be energetic and confident. I love good dates, but I can enjoy bad ones too. The moments when disaster appears imminent and you can almost hear the clackety-clack of the rollercoaster climbing the hill before gaining speed and sliding off the rails. Friends have always found my stories interesting and told me that I need to chronicle my dating and relationship misadventures. 

WARNING: Reader discretion is advised, as I get into some delicate descriptions of encounters that might trigger some readers. If you are easily offended (or went out with me once), please stop reading now.

Here goes: 

bad date stories

Me on a date. One going so badly that I just have to grin and get through it.

Waiter, Check Please…

I was at dinner with my date. I felt playful and texted her a flirtatious message. Her phone vibrated. It was facing up, and I saw on her smartphone screen a notification message that she had me listed in her contacts as “free food dude.”

What a Lovely Adam’s Apple You Have…

The knockout gorgeous fox I found on an online dating site… she waited until after I gave a passionate kiss goodnight at the end of the date to tell me about the hormones and “her” operation. Now, I am totally fine with trans people, but I’m just sayin’ that a pre-emptive head’s up would have been nice. She was a knockout, for sure. Used to be one of the female impersonators in the fashion show at Alan Golds bar before the ole snip snip, although I didn’t know it at the time. I would have dated her again if she had not turned out to be married to her former gay lover. D’oh!

Catfish Story #1

It wasn’t really a date for me — but it was for her. Someone contacted me about collaborating on a photo shoot, sending me a photo of a 6-foot slender goddess in a bikini claiming it was her. I arrived to find a little person, possible three-and-a-half feet tall, her body twisted by cerebral palsy or some other condition. It was so surreal having this person wave me down, introducing herself as the voice I had exchanged a call with earlier, and not saying a word about the situation until about a half-hour in when she expressed appreciation for me not being a dick about it and politely accommodating her. She explained that she’s very lonely and does not get to go out with men, that the only way to share the company of one was to trick him into thinking he was going to meet with this tall, beautiful woman. I smiled and tried to be friendly and show her a good time, shrugging it off as no big deal. We shared a hug before parting ways, and I never heard from her again. It was truly one of the saddest things I’ve ever encountered personally, and I’ve tried to be conscious of what it must be like to live with a disability. If I developed some illness that affected my ability to work or my mobility, would the woman in my life stick around or run like hell? I dunno. I don’t have much faith in people these days.

I Needed to Go Shopping for New Sheets Anyway

bad date storiesI took another woman out on a romantic dinner and she got totally wasted before the entree arrived. Her stuff was at my house, so we had to go back for it. I ended up holding her hair while she hovered over my toilet puking, then she insisted on trying to kiss me. I was helping her to the doorway when she said that she urgently needed to lay down for a minute. Then she fell asleep, snoring like a freight train. I wound up sitting on my couch, eating cereal while my date was passed out in my bed in a vomit-stained dress. Yes, it did get smeared on my sheets, but I wasn’t about to take the clothes off a woman who would have no recollection of what happened for her to be stripped down to her bra and panties in a stranger’s bed. I knew that even before the #MeToo movement started.

The Business Proposition

This next one, surely this has happened to other guys too. I met an absolutely stunning woman on Tinder, and we met up at an expensive restaurant and hit it off amazingly well. A little TOO well. She offered me a line of credit to take advantage of her services as a professional escort. Told her “no thanks” and would not have taken the date if I knew she was fishing for a new client, but I wasn’t judging her choices. She smiled and said I was sweet. In talking, we had a lot in common and remained friends. She liked that I was a nice guy who didn’t treat her like a piece of meat, and I just found her endlessly fascinating in a sort of research way (I write fiction, so how many chances do you get to study characters like the hooker with the heart of gold in actual life?). Being friends with her meant receiving texts during breaks in her weekend getaways with various Sugar Daddies to tell me how physically repulsive and verbally abusive they were. During a romantic dry spell, I considered working out some arrangement with her, but then I’d picture all of those pasty white bellies slapping against her skinny little body and the lust would just evaporate. No, I never let her see my own pasty white belly, although I’d be lying if I said that the temptation didn’t exist. Maybe I was just too lazy to go get tested for STDs every couple of weeks, and she never offered to quit and make me her boyfriend. Last I heard of her, she’s still working those “seeking arrangement” websites. A girl’s gotta eat…

The Competition…

bad date storiesGotta add to this list the “friend” of a lady I had a brief relationship with who got competitive and wanted to prove that she could have me just as easily. Except, I never “had” her in the Biblical sense. She just wanted to be seen with me so she could flaunt it in the other woman’s face that she could get the same guy. Really pretty lady and flirted like a mother-effer, but every time I tried to kiss her, she acted like I was offering her a turd sandwich from a dirty ashtray.

I’m Useful for Something, at least…

Another Tinder date: I met her at Bud’s Sports Bar for a get-to-know-you sesh after talking briefly online. Classy broad, for sure. It was going ok, then her friends showed up along with some other guy she knew. She ordered a top-shelf mixed drink, then another, then another, then another. I try not to be a cheapskate, but I’m feeling like an accountant doing the calculations in my head. This other guy looked like he wanted to rip my head off and shit down my neck. He had a vein bulging in his neck. So she starts talking to him and they walk off together. I figure he’s an ex or something and she’s telling him to chill. They came back and she started openly flirting with him in front of me to the point to where I was being completely ignored. Then she lays a big kiss on him! One of her friends, sensing my bewilderment, admitted to me that the other guy was her newly ex-boyfriend, and I was there solely to make him jealous. I put a $20 bill on the table to cover my empty beers and left.


Not My Proudest Moment

bad date stories

Ladies Man? Hardly.

Back before I got married, I was a single dude on the lookout for a girl to settle down with and make babies. There was no such thing as online dating to humiliate people, so I had to achieve it the old-fashioned way. I was in my early 20s, moved back in with the folks after college. I went out to The American Legion in Gadsden, Alabama with some friends from the Jaycees. It was kind of a redneck place, but we were having fun and dancing. I wasn’t prowling the place in a desperate search for “the one,” just trying to have fun. I danced with probably 5 or 6 different women. Including one who approached me, told me I looked fun and asked me to dance. Well, about 10 seconds later, this Bubba shoves me and tells me to “get the hell off of” his woman. He’s drunker than shit and several people get between us, realizing he’s a freight train of trouble and I’m a 120-pound guy who has never thrown a punch in his life. They get tossed out of the place. I’m shaken. My friends and I hang out for a bit longer, and when we think enough time has passed for the coast to be clear, we leave. Stepping into the parking lot, we see him with his shirt off (it’s February, mind you), pacing around in circles and smacking himself. He is not amused to see me. His lady tries to get between us and he grabs her by the side of the head and beats her so hard she staggers backward, landing on her bony ass. He’s going after her and striking her again and again. A smart man would have seized the distraction, but I couldn’t stand by. I had a sudden burst of bravery and stepped forward, ordering him to stop it. My hands were up trying to talk some sense into the guy, and before I knew what hit me, he knocked me to the ground with one punch. I’m down. They take off, nearly running over me as I lay bleeding on the ground. My friends take me to the emergency room with a broken nose. For years afterward, I will suffer from a deviated septum that requires surgery to correct. The worst part was the next morning, dragging into the kitchen of my parents’ house with two black eyes. I’ll never forget the look on my momma’s face: that injured me more than any drunken redneck brawl at the American Legion on a Saturday night ever could.

The Divorcee in Waiting

The woman I had a fling with despite her still technically being married. Told me they were only living together in the same house for financial reasons and would be divorcing as soon as they could afford to. After a few months of discreet fun, she pretended not to know me upon encountering one of her husband’s coworkers out in public. I didn’t realize what was going on until she’d led me on for months thinking we had a shot to be together again. I kept messaging her like some idiot who didn’t get the memo.


Now That’s Just Bad Timing…

The date where she saw her father leaving the restaurant with a woman who wasn’t her mother… while her parents were still married. Thanks for killing the mood, pops.

The Giver…

The stunning, seemingly refined and sophisticated woman I met online who was really wasted drunk and wearing sexy lingerie when I showed up at her place to take her out to dinner. At the moment, I didn’t know what was going on. She was in a manic depressive state, alternating between trying to stick her tongue down my throat and threatening to stab me in the neck with a wine corkscrew while declaring that she was disgusted by men in general and was going to “show” me what happens to players who seduce and then abandon women. It was schizophrenic, and I thought either she’s playing games or she’s crazier than hell. She stood between me and the door holding the corkscrew. I grabbed her wrists, twisted around so my back was to the door and promptly escaped her apartment. I darted to my car as she screamed from the stairwell that I had some nerve thinking I could just do whatever I wanted. She left 6 drunken messages on my voicemail, her words slurred, alternately threatening bodily harm and volunteering to sleep with me. I listened to the voicemails while sitting in line at the Krispy Kreme drive-through (I needed comfort food after that). A couple of days later, after I failed to return any of her calls or text messages apologizing for that shitshow, she sent an unsolicited package to my address that she found after stalking me online. Ironically, her peace offering was a bottle of wine… and a corkscrew.

The Reunion...

The woman I was friends with in high school who seemed to be everything I could possibly want: smart, pretty, petite, feisty, fun. From our first date, we were so good together. The chemistry was powerful. Unfortunately, I hadn’t been divorced for very long and was still in my selfish phase, so I I always seemed to end up being with her during small chunks of time when the man she wanted to propose to her repeatedly cheated on her. She kept going back to him, and eventually, he grudgingly DID ask her to marry him — before inevitably cheating on her again. She repeatedly told me she wanted a serious relationship leading to marriage. After I finally, at long last, said yes to the commitment thing, she freaked out and started “ghosting” me. Explained that she didn’t think I was as serious as she was about being together. Then she immediately unfriended me on Facebook and blocked me.

Past My Prime

bad date stories

I have a knack for attracting, um, “interesting” people.

Oh, and then there was the college student I met on Tinder and took to dinner and the karaoke bar Sing It or Wing It. She greeted one of her sorority sisters who didn’t even bother to lower her voice to say, “Ewww. He’s so OLD…” When we stepped outside to smoke she pulled me close and kissed me. She’s cute, but nuts, and drunk, and I would rather be anywhere else, and yet I was fascinated by where this is going because she’s young enough to be my daughter’s older babysitter. We sat up all night. Wouldn’t allow me to touch her below the neck, but also wouldn’t leave, so I basically laid there listening to her talk endlessly. I had never been happier for someone to go home so I could have my bed to myself and sleep.

The Ultimatum…

Sometimes I do make it past a first date, only to find brick walls a little further ahead. I started seeing a woman in Chattanooga a couple of years ago. I guess I spent every spare minute with her when I wasn’t at work or making the hour-long commute to and from Fort Payne (where I have joint custody of my daughter). After a few weeks of this, she told me that she didn’t like that I was gone half the time and I needed to spend more time with her and less with my daughter. I shouldn’t have to tell you how quickly I told her to go to Hell.


Occupational Hazards…

On another first date among so many, the woman randomly asked me if I had ever dated anyone I worked with, then opened up to me about how she works with her ex-husband and how hard it is to see him every day and how much she hopes they can get back together someday. I was kind of stunned by all this and finally just said “If you want to get back together with your ex, why am I here?” and she said, “I keep trying to make myself date other people to try to forget about him, but it never works.”

The Sad One…

I met Andie through a mutual friend. He had the hots for her but she and I just clicked instantly. She made it known to me that she just liked him as a friend and was attracted to me. So this drove a wedge between my buddy and I, as he resented me taking up with a lady he knew that I knew he liked as more than a friend. Andie and I hadn’t been seeing each other very long when she was diagnosed with breast cancer. I offered support and encouragement, but I really didn’t know her well enough to stay at her bedside the whole time like a full-fledged boyfriend. Maybe I should have, but our mutual friend had started coming to visit her a lot and it would have been really awkward to bump into him when he was still raw at me. I spent a lot of time talking with her on the phone about her disease and chemo. I tried to encourage her to call me whenever she was scared and needed a friend to talk to. Then she just out of nowhere died so randomly on a Tuesday afternoon. So sad how quickly it just overtook her before she could even put up much of a fight.


Refer Madness…

In telling the tale of my many bad dates, I can’t leave out the hippie I met on Plenty of Fish who welcomed me into her living room and pulled out a gigantic bong to take a hit before we left for dinner. (I’m generally free spirit & 420 friendly, but in the first 2 minutes of meeting someone?!) She told me that she just got dumped because her ex found her to be “too clingy, but there’s no such thing if you really love someone…” I kept looking around for hidden cameras in case I was on one of those TV shows. It was so bad that I admitted there on the spot that we were not a match and I would save us both time by leaving. The only time I’ve ever done that.


Oh, and there was a woman who lived with her parents in her 40s. Granted, she was picking up the pieces after a divorce where the guy just basically left her high and dry with a lot of debt, but still… Her father grilled me as if she were 16. Dude, I am totally going to sexytime your daughter. Under your roof. Like it’s prom night, daddy-o! I didn’t. Turns out, age was the only thing we had in common.

The Cinema, Part One…

The one from Birmingham who randomly opened up about how she had been molested as a child during dinner conversation. She became aggravated when I did not reciprocate with some deep, dark secret of my own. We saw “The Girl with the Dragon Tattoo.” Nothing like sitting next to a triggered survivor of sexual abuse watching anal rape scenes.


The Cinema, Part Deux…

Also in Birmingham, a different woman I met on Tinder seemed cold and awkward during dinner. I remarked that the night was still young (kinda hoping she would want to call it an early night). We went to that same movie theater. I love Natalie Portman, so we went to see her new movie called “Black Swan.” Normally, I’m all about watching Natalie doing lewd things on the screen with Mila Kunis. But on a first date with a woman with whom I share zero chemistry?! AWK-WARD… She was so creeped out that we left early and she didn’t give me a goodnight hug or kiss. A handshake, as I recall.


The Pool Party

My friend in Rome, Georgia, had a lot of fun friends. I saw where one of his friends was pretty and had a fun attitude. I sent her a friend request because she was single and attractive. She invited me over to meet her in Rome. Drove an hour and arrived to find a dozen or so of her friends at her place having a wild-ass pool party. I had no swimsuit, so I was just this weird, nearly sober stranger in the corner being ignored. Finally, she walked over and suggested that I leave because nothing was going to happen between us, the implication being that I was the only person there failing to recognize that she was clearly out of my league. I tried not to take it personally, but DAMN! I guess she didn’t care if my feelings got hurt because I was absolutely no one to her.


DTF… Just Sign on the Dotted Line

You know how women are always complaining about rude guys sending dick pics? Well, this one woman I met on Tinder sent me a photo of her vagina within 5 minutes of chatting, apparently wanting to show me how youthful and pretty her labia is. Now, men tend to react a bit differently to unsolicited nudes than the ladies, and let’s say my curiosity was perked for purely lazy reasons. Don’t judge me. This did not seem like it would be a difficult hill to climb and plant my flag at the summit. What’s a little harmless fun if you use protection, right? So imagine my surprise when she insisted that I had to commit to a long-term relationship in order for her to give me “privileges.” When she insisted that she wasn’t talking about marriage, just a small commitment ceremony with only the two of us there, I said, “Lady, I’m Out…

The One I Put in the Hospital, Part One…

I knew this girl when she was in high school and I was just a few years out of college. Decades later, after she’d spent years out west modeling, she returned to Tennessee. I didn’t know the full story. I just knew that she’d recently broken up with her guy, so I asked her out. To my surprise, she agreed and we went out to dinner. We had a fascinating dinner conversation about some shady characters she got associated with while she was in LA. doing the hot-girl-in-LA thing.  I’ll spare you all of the gory details but let’s just say that during our date, she started bleeding. Down there. And not in the way women usually bleed down there. I was genuinely concerned for her and drove her to the ER. Her parents arrived and looked at me like I was some kind of monster. I think they would have called the police on me if she had passed out from the blood loss instead of explaining that I was not the cause of it. Turns out, her ex-had beaten her pretty badly, hence her reason for leaving him. In our playfulness, she reinjured some of her internal organs enough to bleed. Despite that night ending rather horribly, I tried to get her to go out with me again, but she found Jesus and concluded I was a sinner or something. Last time we exchanged messages, she said she’d pray for me.

 The One I Put in the Hospital, Part Two…

We were a perfect couple on paper and really hit it off. Didn’t try to kiss her at the end of our date because I didn’t wanna rush it. A few days later, I messaged her and asked if she’d like to go out again. She responded with a picture of herself in a hospital gown, saying she had hurt her back really badly since our date, could barely move and wouldn’t be going anywhere for a while. Seriously, am I cursed?

The Journalist…

Very recently, I had a lovely evening with a woman I met on Tinder at a swanky Italian restaurant. It went very well, and I woke up the next morning excited by the prospect of seeing her again. I cranked up my laptop and visited Facebook to find that she had written a lengthy post about the whole date on her Facebook wall, complete with excerpts from a privileged conversation that was distorted to make me look like a real jerk pressuring her to have sex on the first date (it was a general conversation about arbitrary rules, i.e., three dates vs six, etc.). She closed her Facebook post with the words “I will continue dating myself.” I did not take that as encouraging. Later that day, when I told her how uncool this was, she insisted that I had misinterpreted her words, but she pretty much told me off because when explaining my reaction, I said that she had “journaled” our date. She said this hurt her deeply. She is a writer, dammit, and accusing her of merely journaling belittled her. She said that if we had dated, I would just have to get used to her spilling our private conversations onto her prose (I hope that in the book she at least has the decency to give me a huge you-know-what, even though we did not have sex, thank God!). I think it is only fair that I should be able to mention our encounter on my blog since she’s already warned me that I’m going in her forthcoming book! It never would have worked out because she was a very blunt Northerner who had insulted my choice of clothes in the first 5 minutes of the date. I’ve been single for too long now to put up with that kind of crap.


Judge and Jury

Another woman I advanced beyond the first date with just couldn’t get past the fact that I am a photographer who has shot calendars with swimwear models and kept texting after our date to lecture me about how I must have slept with all of those women and how they were too skinny and I probably forced them to starve themselves and called them “whores and sluts” and asked me what did I have against “real women” like her? That one was doomed from the moment she showed the depth of her insecurities.


The Devil Worshipping Cokehead…

Last but definitely not least, I can’t leave out the woman I met on Facebook through mutual acquaintances who had repeatedly asked me out, then vanished from Facebook, then reappeared some months later. Repeat cycle. Finally got together for real. Said she didn’t want to drive after having drinks and was fine crashing at my place (oh hell yeah, am I right?). Wouldn’t shut up talking about religion on the 25-minute ride to the restaurant. Got some shots of Fireball in her and then she revealed that she’d been involuntarily committed to mental institutions twice in the last 3 years. Babbled on cryptic shit about how she got involved in a Satanic cult that wanted her to ritually sacrifice her infant son while she was sprawled out naked on an altar, but the apparition of her dead father appeared before her and told her not to grab that youngun and scram. The server at Taco Mac kept coming by whenever she excused herself to go to the bathroom after I shared some of the crazy shit she was saying. She alternated between trying to stick her tongue down my throat and speaking in tongues like a Pentecostal on PCP. At one point, she stopped in mid-sentence, looked at me with an evil glare and said, “When did you sell YOUR soul?” Switched to a different personality and begged me to take her to meet some guy 30 miles away to buy some crack cocaine. I stopped by my apartment, got her overnight bag and took her crazy ass home. As I pulled out of her driveway, I could see her backing her car out, going to meet her drug dealer. I honestly couldn’t tell you whether she survived that night unscathed or got locked away on a 5150 hold.

In Their Defense…

Alright, at this point I know it looks like I’m just a magnet for insanity and bad luck. I certainly feel that way. And for all of the loonies and flakes I’ve encountered in my romantic travels, I’ve also met some of the most amazing women I could ever hope to know. I have a handful of really close female friends that I originally met on online dating apps, and it just didn’t ripen into relationships or my ass was too selfish or too stupid to pursue them once I had my chance.

In defense of these aforementioned ladies, I’m sure they would tell you their version of the story and likely not seem as far off the reservation as they appear from my perspective. There are probably a few people who include me in their own bad date stories. I’m far from perfect and probably self-sabotage a good thing once I get nervous that it may lead somewhere.

A post-mortem on my Love Life

I think I’m done looking for love.

Despite all of these attempts to discover a relationship worth pursuing, I’d describe myself as still relatively inexperienced in dating since I did not do much of it as a teenager (I was very shy and infatuated with one girl from Kindergarten until about 10th grade), then I got married for 15 years. Getting back into the dating pool in my 40s was a bit like treading water among sharks. Or more accurately, sometimes I was the shark, other times I’ve been the chum.

In telling these stories, I’m sure you’ve learned a few things about me, not all of them flattering. Yes, I’m not a virgin. Duh. Talking about it is kinda embarrassing. I’m basically reliving a lot of humilating experiences. I dunno. I may delete this blog before the day is done.

I’ve seen people I really like become people who no longer talk to me. That’s the unfortunate part. Just yesterday, I noticed that a woman I really like had changed her Facebook status to single. I like her so much, but I can already hear her saying, “Ah thank you, that’s flattering, but…” and growing distant until she’s completely vanished from my world.

When I walk outside and look at all the people walking around, it’s sort of weird to know that some of them act like normal people, yet some of them have just completely twisted mindsets as they walk and breathe and breed among us. Anyone you see walking down the street could be racist, sexist, or any sort of depraved freak, yet from the small talk they engage in, they seem normal. I’m certainly not normal. I’ve concluded that I probably have a touch of Asperger’s. Social situations have always been excruciating for me. I’d probably have a lot better stories (outcomes) if I had not so often deferred to others to approach me and take the initiative first.

Will I ever find love? Will I die alone? I hope not, but I’ve grown content being alone. It’s not completely without its perks.

What’s been your worst date ever? I’d love to hear your story.