In which I answer a random question generated by a website. Here’s this week’s question Feel free to give your own answers in the comments.
What was the worst date that you’ve ever been on?
This one has two completely different answers, because I’ve been on two really bad dates that I can still remember, but for completely different reasons. One turned out bad as in “get the hell out of my life” bad. The other turned out bad as in “well, that experience wasn’t the greatest, but…”
I’ll start with the bad-bad date, which happened about six months before the bad-good date. It was around Thanksgiving, and friends of mine decided — since I’d ended a long term relationship about six months before this — that they’d fix me up with a friend of theirs, saying that we were perfect for each other, and so on.
So we both met at a holiday party, and I was immediately not really interested. I don’t even remember his name or his face. But he was persistent, and one thing I lacked at the time was resistance. I didn’t really know how to say “No.” So he dragged me into a bedroom, we made out, he did show me a couple of things I hadn’t experienced before, and then we wound up making out in my car.
Yeah, I know. I shouldn’t have ever let it get to that point, but I did. And then he asked if I wanted to go out, and I stupidly agreed. Yes, the quickest way to a man’s heart is… not through his stomach.
We arranged a date for a weekend not long after. A couple of things to point out. During the party, I had mentioned that I didn’t have a Christmas tree because I didn’t want one and didn’t do that sort of thing because I thought it was stupid and a waste of a perfectly good tree, and anyway I don’t really celebrate Christmas and never decorate for it.
So… he shows up at my place with a potted mini-pine with LED lights all over it, because he thinks it’s sad that I don’t have a Christmas tree. Okay, missed signal number one. Next, he takes me to dinner at some really fancy, really over-priced restaurant in WeHo, insists that it’s his treat, and proceeds to basically break the bank on everything.
He orders expensive shit for himself. He orders expensive shit for me. And oh does he start going through the drinks. Well, for him. I’m not having anything stronger than Coke (as in -a-Cola). But he has one cocktail after another, and there are appetizers and entrees and aperitifs and salads and coffee and dessert and who knows what else, and I can’t help but notice when the check comes that he’s spent damn near four hundred bucks, not including tip.
And the only thing I can think is, “Wow. I am so fucking unimpressed.”
Why? Well, first, I’m not a whore. If I were, I would have skipped dinner and said exactly how much it would have cost to do what to which part of me. Second, there really wasn’t a lot of “getting to know you” time involved during this whole snarf fest despite the time it took. There was a lot of “This is about me,” and “Here’s what I think about you.” And while the latter part was complimentary, it really wasn’t making a connection.
But then the dinner part ended and thank god I drove, because he was tanked, and when we got back to my place and because of my unfortunate young and naïve inability to say no (I bet the women reading this can relate) I felt obligated to invite him up and… yeah. Bad sex ensued. Really bad.
What made it bad, besides “everything?” Well, let’s just say that he was not really well-endowed (not necessarily a big deal, because I’m an ass-man), but that he insisted on wearing a cock-ring and, more annoying, kept doing the late 90s version of (long since illegal) poppers, which was a small bottle of video recorder head cleaner that he’d sniff. And he tried to get me to sniff, although I at least told him in no uncertain terms that it wasn’t going to happen, even when he tried to sneak it under my nose.
Funny how I could easily say no to drugs, but not to sex, right?
Ultimately, I came, he went, and I never gave him a second chance. The scary part was a month or so later when one of the friends who’d set us up called me and apologized profusely. Apparently, the guy they’d set me up with A) Had a boyfriend at the time, B) Was using that boyfriend’s credit cards to pay for the whole date, and C) Didn’t know that his boyfriend had killed his own former boyfriend, and it was dead boyfriend’s credit cards the guy I went out with had been given.
So… WTF? Oh yeah, the topper? Murderous boyfriend lived next door to me.
I dare anyone in the comments to top that as worst date ever. At least I never heard from Bad Date Dude again, and never wound up on boyfriend killer’s radar, although I think he was arrested not long after the whole fiasco.
Here’s the palate cleanser, though, because a “bad” date I had six months after that turned out to be a really good one.
I was at a coffee shop down the hill from where I lived. It was April 29, a Saturday. A friend of mine — who, oddly enough, was also a friend of the friend who’d set me up on disaster date — came in with a woman and man I didn’t know. They saw me, we waved, and after they got their stuff, they came to sit with me.
And all I could think, looking at the guy with them, was, “Holy shit, he’s cute.” And I do remember his name. Steve.
Anyway, the four of us hung out for a while and talked but, big shy dumbfuck I was at the time, I didn’t really talk a whole lot to Steve, just listened as he was talking to the others, but when it came to trying to connect, nothing. And I went home kicking myself, but later on I called my friend, Dan, and asked him.
Now, as it turned out, Steve was a friend of the woman in the group, Michelle, who was a friend of Dan’s, so this was a friend of a friend of a friend thing in both directions. And when I called Dan and said, “So, hey, what do you know about Steve?” He told me that Steve had already called Michelle and asked her what she knew about me. She didn’t, so she had already called Dan… bing. So Dan gave me Steve’s number, I called him up, and we talked for three hours.
We set our first date not long after — Friday, May 5th -— and damn did everything go pear-shaped. He had planned for us to go to an L.A. Philharmonic concert at the Hollywood Bowl, so we drove out there only to discover that… the Bowl was dark, because the Phil at the time was still performing in DTLA, and summer concerts at the Bowl were still a month or so off. There was also no way to make it downtown before at least the end of the first half.
Well, okay. Then let’s go get dinner. And, since I’d been working for a local LGBTQ+ publishing company that had just compiled a local restaurant guide (as in I’d just gathered a bunch of listings) I knew of a highly rated place we could go. So we went, and got there, and found out… No. It’s already gone out of business.
And there were a couple more failed attempts along the way, but the funny thing was that as we went along on this adventure, we talked to each other, got to know each other, and by the end of the evening, it wouldn’t have mattered if our first date meal turned out to be day-old donuts we fished out of a back-alley dumpster. All that would have mattered was that we were doing it together.
We eventually wound up at some restaurant in WeHo, had dinner, then headed back to his place, probably rented a DVD, and then had amazing sex. And it turned into a long-term relationship that eventually ended for the stupidest of reasons, but we’re still friends to this day.
But I still can’t remember the name of bad-bad date guy to save my life.
So there’s a tale of two worst dates. One the worst because of who I was with and why I went on it. The other the “worst” because I wanted so much more for whom I went on it with, but wound up getting exactly that.
That was the real lesson, though. The only thing that makes it a bad date is the wrong person. It you’re with the right person, then no way will it ever be a bad date. If you’re with the right person, the Ninth Circle of Hell is Heaven. Hell, (pun intended) with the right person, it’d be time to go ice-skating.