So, Who Has A Weird First Date Story?

Oh, I do! I guess after Valentine’s Day and all the talk about love and romance and barf, I’ve been thinking about first dates. So I thought maybe we could do a weird first date-off! I’ll go first, but please share your stories in the comments.

My first date with the dude who would become Mr. McDoogal was actually my only first date ever. I was 22 and had only been single for a few months after being dumped by my high school BF. This date was kind of destined for awkwardness because I didn’t know how to act. Later, I would learn that he actually liked my straightforward manner, when the truth was I just had no idea what I was doing.

Things started off easily enough: a quick handshake and we headed into Starbucks (I know). Since it was summer, we both got iced drinks, and on the way out the door, he tilted his drink toward me. A normal person would assume (correctly) that he was doing kind of a friendly “cheers!” thing, but I thought he was offering me a sip and I took a sip of his drink. Fortunately for me, he just kind of half-laughed and we moved on and I managed not to run away screaming and/or exploding from embarrassment.

So an hour or two later, he walked me to the door of my apartment building, and we stood on the sidewalk doing that “awkward extended goodbye; interested in you but sorry, not inviting you up” thing. My reasons for not inviting him up, by the way, were twofold: I was still smarting from the breakup and didn’t want rush into things, and I wasn’t ready for him to see my messy apartment and slightly-embarrassing geriatric pet hamster.

(An important sidebar here is that my spouse has kind of an angel face; strangers of all stripes find him very approachable. I didn’t know this yet, but I was about to learn.)

After a few minutes of talking and not making out, we heard a car pull up right next to us. Now, I lived in a cute neighborhood in a nice town right outside Washington, DC, so there was usually nothing to worry about, but it was late and there weren’t any other cars around, so we both took immediate notice. It was a guy, alone in a pickup truck, and as he rolled down his window and leaned over the passenger seat, I reflexively took a step backward.

The guy asked Mr. McD for some money for gas, and he truthfully answered that he didn’t have any cash. (These were the days when we never had cash on us, because having cash meant you actually had real money.) I thought it was weird enough that someone driving a car was panhandling, but it was about to get weirder.

“I just, I really need some cash, man. I hate to say this in front of your lady friend here” – which, by the way, lady friend, like it was the freaking 1950s – “but a bunch of guys just jumped me and they took my wallet, everything. They took my pants, man.” It was almost seven years ago, but I still remember his exact wording: They took my pants, man. He then gestured for Dave to look to confirm that he, indeed, was without trousers.

But ascertaining that his pants were missing just raised more questions than it answered. Who were these hooligans? Where were they now? What had made them decide to go jumping people and stealing pants in a quiet residential area? Why did they bother taking his pants when they could easily have just taken his wallet? Why did this guy go driving down a nearly empty street trying to beg for money when what he really should have been doing was going to the police station?

I don’t know, guys. Maybe they were nice pants. Maybe these were people he had planned on engaging in some sexytime with but things went horribly wrong. Maybe he was lying, and he’d lost his pants some other way. Maybe he was high. OK, no, he was definitely high. The point is, it was with heavy hearts that we had to send him on his way without any money and without his precious pants.

The only silver lining, I suppose, was that my sip-taking faux pas ending up not being the most memorable thing about our first date. And after that, a laugh, a shrug, and a hug goodnight didn’t feel nearly as awkward as it probably would have without that little icebreaker. So thank you, pantsless man. I hope wherever you are now, your ass is wrapped in beautiful fabric.

95 replies on “So, Who Has A Weird First Date Story?”

Nothing too terrible, but this post is making me relive all these cringe-worthy moments from my younger years when I was desperate for male attention (Ages 13-20ish).  Despite a fairly supportive and progressive up bringing.  I’d like to think I’m past it now.

When I was 13 I somehow managed to snag the lukewarm affections of the new kid, who had just moved to California from Florida.  Looking back, we were both chubby insecure kids with bad haircuts, but at the time having someone who ‘liked’ you was so very validating for my fledgling self esteem.  We spent one lunch period playing racket ball together, and I accidentally swung my racket back too far and decked him.  Splitting his eyebrow so badly he needed stitches.

The next one that comes to mind is from OKcupid.  Myself, being utterly incapable at age 18 of actually meeting people in real life.  He picked me up and was substantially older and shorter than the profile indicated, and clearly incredibly nervous.  I had to walk up a long flight of stairs where he was pacing back and forth and I stopped dead, seriously considering turning around and walking back to my dorm.  He had spotted me so there was no turning back.  He asked for restaurant recommendations and I insisted forcibly on coffee.  He was trying to break the tension on the ride down the hill and with painfully forced playfulness encircled my thigh with his hand.  I recoiled so much I was plastered against the passenger window.  The date was long and awkward.  The next day he emailed me saying he was sorry and not very good with people, asking for tips and genuinely apologetic.

I said no for a good two weeks because I thought it was a joke. When we did go out, I was so nervous I randomly blurted out halfway through, “I’m not going to have sex with you, and I don’t really like touching people full stop. Actually I don’t like people at all. Sorry.”

To his credit, he wasn’t bothered.

As it turned out, it was just non-horny me who didn’t like people. Go figure, eh?

I am actually still majorly anti-PDA though, like a proper Brit. I feel sorry for anyone trying to date one of us who doesn’t get it – all couples here look like they hate each other.

Hahahaha I love that. You can easily recognize tourists in England, they’re the touchy kind. This is why I claim being English through being part of the Commonwealth, I only like to be touched by those I love, not random hugs, kisses, hand shakes and prods. And in private of course.

I was set up with a guy by his mother, who thought I was wonderful.  She was well-to-do, refined, elegant.  Surely her son must be wonderful!  I realized later, she hoped I could unfuck her son. 

Date: brunch in Malibu.  He shows up in a dirty pickup truck.  (Understand this is LA in 1990 – no one was driving pickups or SUVs at that time.)  We went to a restaurant which served freshly made juice.  He asked what the watermelon juice tasted like (watermelons, I would think) and demanded the waitress make a sample for him.  She was reluctant so he dropped his ace in the hole - he was a friend of Charlie Sheen’s, part owner of the restaurant.  He asked for the manager to whom he made much of this connection.  Upon  drinking the sample, he got a watermelon-juice-mustache.  This is not cute like a “got milk ad.  He didn’t wipe his lip for a looonnngg time. 

All the while, he bragged about his acquaintance with Charlie Sheen.  This guy was about 30, living with his mom, no college education and sold meat wholesale for a living (after an extended period of unexplained unemployement).  After “regaling” me about Charlie Sheen for much too long, we left the restaurant.  He made a left turn across the Pacific Coast Highway in between traffic lights, on a Sunday.  You must imagine heavy, fast traffic.  I’m not sure if he even looked before he pulled out.  I closed my eyes, because the car I was sure was going to hit us was headed for my side of the truck!  There were several cars honking, squealing brakes and, luckily, no impact.

This date was so bad it was nearly FATAL for me!

I didn’t date a lot and more of those weren’t funny, but I think the start of my relationship with le bf could be a story.

We met online and the first time ’round we wanted to meet offline was because he offered me to take me to the zoo for cheap (and I’m cheap). But: the zoo had two entrances. The old one (and known to locals as the only one) and the new one (where the bus dropped you off). Le bf wasn’t from around and waited for me at the new one. I didn’t even count the new one as an entrance and I waited at the old one. And we had forgotten to exchange numbers (because meeting up with an online stranger is fine. Giving him your number? Na-ah).

We didn’t meet that day. How we came together is another story.

Weirdest Date: I was still in high school (maybe 17 yo). A friend of mine, S, sets up a double date with her guy, A, and his friend, B. B is driving and picks us up. But then he tells us that he has to go pick up his grandma who is gambling at the casino (~ 45 min away). Kind of weird date activity, but whatever. He promises we’ll do something fun later. After dropping off his grandma, the guys recommending renting a hotel room for a few hours of drinking (this was a somewhat common activity for us underageds who couldn’t go to a bar).

So far I’m thinking B seems nice enough, but no chemistry. After drinking for a little while in the rental, S and A go to the bathroom to (I guess) hook up. And B takes that as his cue to put on some porn. I was questioning to myself, “Is he coming on to me?” because he hadn’t been flirtatious at all. Then he exclaims, “It’s hot in here!” and strips down to his boxers and lays on the bed next to me. I just sat there, feeling oh so awkward. I still am not sure if that was his way of flirting or if he wanted to give the impression that we hooked up? Later on, S told me that B wanted to go out again and he was “sorry he came on too strong.”

But that wasn’t my worst date…

Worst Date: He talks about money A LOT. He works some kind of sales job. He asks me, “Do you know what the secret to being rich is?” (Disclaimer: he wasn’t rich.) He tells me the secret to being rich is never “settling for a set wage.” I tell him that I must be well on my way since I had worked as a waitress for over 5 years at that point. He does not get my attempt at humor. He keeps telling me how he loves buying presents and spending money on people he likes and asks me if I want him to buy me an iPod. And he asks me where I’d like to go on a vacation with him. I tell him that I like to know a person better before I accept gifts or vacations from him. The icing on the cake was when he asks if I had a boyfriend. I respond, “No, why would I go on a date if I was with someone?… Oh.. Are YOU with someone?” He tells me that, yes, he has a girlfriend. But it’s okay because she’s out of town, and besides, things weren’t going  that well.

They took my pants, man.

Oh my god, I love it. Some combo of the haplessness and the “man” and the fact that he was high makes me imagine the guy as The Dude. All The Dude wanted was his pants back!


First date with my fiance was amazingly awkward even though we’d been acquaintances for years and had never had an awkward moment between us.  We were sitting at a rather large booth at a bar, and I got there first, and he sat aaaallll the way at the other end when he got there and could barely look at me until his second drink (later he would tell me he “used up” all his courage in asking me out). Even though he had asked me out, I suddenly became concerned that it wasn’t in fact a date. But instead of asking him what was up like a reasonable person, I began sidling closer and closer to him over the evening, deciding that if he didn’t move away it was a date. Success!

I’ve told this story here before, I think, but I WILL TELL IT AGAIN.

The reason I am with the current mister is because one of his friends set me up with him without telling me. Yes, without telling me. I had a semi-formal coming up, mentioned I didn’t have a date, which someone else took to mean I WANTED a date, told one girl in the sorority who is known for hooking people up, and she set it all up. I got a phone call from my roommate (the girl was the RA) saying, “Come downstairs, K got you a date for semi!” And I was just like… What? So I went downstairs, I stalked his facebook with them, decided he was cute enough and I would allow it (I didn’t want a date, but she already asked him, so what else was I supposed to do?). I talked to him online and we set up a lunch date to meet before the semi-formal. It was supposed to be a group thing, with me and him, two of his male friends, K, and one of his female friends.

Except all the girls cancelled. And another dude tagged along. So I went on my first date with this guy with three other dudes.

I tried to make small talk on the way over, while we were picking up his friends, while we were standing in line to order, and finally I turned around and said, “Listen, I am not good at talking, I am pretty awkward, I don’t have anymore questions to ask, so if you’d like to say anything, feel free, but if you don’t mind, I’m not going to say anything else.” He laughed at me and said okay. So I didn’t say anything else until he took me back to my dorm.

And somehow, four years and some odd months later, he’s sitting next to me at his desk playing video games (I think the demo of Mass Effect?) while I avoid reading for class (now in grad school). And it’s pretty perfect.

(Sidenote: long time creeper, first time posting. Hi ladies!)

My first ever date was at the tender age of 12, I asked a guy friend B out because i knew from his mom who told my mom that he liked me and i figured why not! His mom drove us to the local cinema, where we proceeded to wander around the mall before the film started (Fantasia 2000 at the IMAX. Why? I don’t know), being nervous and sweaty and nervous. It was fine, as first dates go, except for when we were in the movie itself, slumped over and eating popcorn. And the popcorn kernels fell down my tank top and landed between my budding breasticles, right where my bra seam was,a nd it was rubbing and itchy and uncomfortable. So I tried to discreetly wiggle my shoulders so the kernels would continue to fall down my shirt but nope, no luck. I don’t know how you ladies were at age 12 with the breasts just beginning to grow but i was oh so very awkward and embarassed. But it was so irritating and I couldnt let it go, so ended up having to reach down my shirt and fish out the kernels, and it took several tries to get them all. Poor B, right next to me who had no idea how itchy I was, looked over just in time to see me apparently groping my breasts.
We spent the rest of the date avoiding eye contact, he even stopped trying the sweaty hand holding thing. My poor heart was broken. His mum drove us home in total silence. Poor 12 year old us!

When I was 18, I went a date with this guy from one of my classes. I was looking forward to it, except when he came to pick me up his mom was there. She was driving us to the theater – which I’m understanding about because I don’t have a car and I figure okay, you gotta get there somewhere.

But then she went into the movie theater with us. Again, okay …weird because if you’re going on a date, so you really want the date’s mom to be there? She wanted to see the movie too. It was just awkward because the theater was pretty empty and she sat a few rows behind us. And my date put his arm around me in the most awkward way that pretty much forced me to lean up against him.

Anyway I felt very awkward during the entire movie like ‘Omg is she staring at us?’ and things like that. I didn’t really want to do anything afterward.

I quickly called it quits with this guy because shortly after I missed a class due to a migraine and he called later, asking why I hadn’t been in class that day. When I told him why, he said “I wish you would have told me.” I’m still trying to understand why I would have to tell him.

I was trying to come up with a good story and realized, I haven’t been on very many actual dates. Any relationships or flings I’ve had usually started while I was out somewhere, a dude in earshot was impressed with my witty nonsense (which is to say, I make jokes that get more cerebral with each beer), and we’d have makeouts and sometimes sexy times.

The current dude I met at my favorite bar, and I saw he was reading a very large book, and being an English major I was all, ooh, large book! He reads things with actual words! WE MUST HAVE CONVERSATION! We ended up talking about Ulysses, both surprised that we’d met someone else other than a lit professor who’d actually read the whole thing. I also asked him if he was both straight and single, because I do dumb stuff like that. We fell in love so fast it still feels like yesterday we met, even though it was six months ago. Nothing weird or (too) awkward, but it is something sweet and makes for a good story.

And that’s just the abbreviated version! I didn’t include the bit where he thought my best dude friend and I were dating, and when he said he doesn’t eat meat and I looked at him, aghast, and asked “You mean you don’t eat bacon?”

Then after our first, ah, meeting at my apartment, I thought he was just going to leave and not stay the rest of the night, like I’ve been used to dudes doing for the past couple of years. And he said “Nope, I’m gonna stay,” and I can’t get rid of him now.

This isn’t necessarily a “first date” but it’s the story of how I met me husband:

We went to a very conservative Christian school and were in a night class together — the topic was New Testament Study, and we got extra credit for going to weekly study groups. A few weeks into the semester, I went to study group at a cafe on campus. My husband was in a different study group, but apparently he couldn’t find his, so he crashed mine a few minutes late. Now, he’s in the Army but I didn’t know that at the time and just assumed that he was some sort of athlete (hey, he had muscles!). He’s also kind of shy but I didn’t know THAT either and so I started hassling him for not participating WHATSOEVER in the group discussion (TBH, I initially thought he was a dumb jock type). Like, literally my first (teasing) sentence to him, “Soooo – you plan on contributing anything tonight?”

Thankfully we were at least on the outside of the study group’s booth, because  the two of us just flirted and talked the rest of the night, both contributing absolutely nothing to the study of the New Testament and probably pissing off everyone else in the group.

THEN the places starts flooding. Like, very aggressive jets of water streaming into the cafe, which is in a split-level basement. Things were massively chaotic for a few minutes, with students trying to turn over furniture to stop the place from flooding (they failed, it flooded massively and was closed for several months while the ripped all the flooring out. We got separated and apparently my husband was concerned and looking for me. I guess I was a bit more blithe about it b/c I just found a friend with a car and headed back to my dorm, where somehow ALREADY there was a Facebook message waiting for me. Then all the power went out on campus for the night.

I’ve always wondered how he managed to get back to his room so quickly and send me that message. Oh, also, neither of us ever went to study group again.


In high school, one of my brother’s friends asked me out. We’ll call him A. A invited me to a Halloween party and suggested we go as Ninja Turtles. I was pretty excited but when we got to the party, I discovered it was at the Elks Lodge, we were the only people under 40 and I kid you not, he abandoned me. He was staying the night with my brother that night so unfortunately he was taking me home and not leaving. It was weird and awkward and he kept trying to sneak into my room all night and “talk” with me. I eventually had to be blunt and I told A no, I didn’t want to date him, kiss him, or see him again and he should stop using my brother to come see me. That did the trick and I never saw him again but that wasn’t the last I heard of him; two years later he was thrown in jail because he beat his girlfriend’s baby to death. Apparently he would hit the child while she was at work because it was crying but it was crying because he broke it’s leg, so he threw it against a wall. Glad I dodged that bullet.

The baby in the apartment upstairs of me cries a lot. It doesn’t bother me at all, cuz it’s a baby. Whatever. What bothers me is that there is a large gap of time between when it starts crying and when I hear someone moving around to check on the baby. Sometimes it has gone for for 10-20 minutes.
One time I heard an adult male scream back at the baby. After reading your comment, I’m more worried for the baby.

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