Recently, a friend of mine posted on Facebook asking for stories of bad dates. I knew this was my time to shine since storytelling is (obviously) one of my favorite things to do. Especially when those stories are mostly negative and completely humorous. I tried and tried to think about the worst date I had been on and, to my surprise, none of them were that bad. Honestly, I haven’t been on many dates, and the ones I have been on have mostly been mediocre. I settled on a story of what I considered my “worst” date, a date that was bad because I made it that way. But thinking about all the boys that I have been on dates with got me thinking about something new: a date series.
So here it is: I’m going to take all you readers (all three of you) on a journey through my dating life, bad and good, starting in 2012. I have a surprisingly detailed memory when I really set my mind to it, so these stories will likely be a lot more drawn out than they need to be. Hopefully it’s somewhat entertaining.
Dating without Expiating LA: Richard
The same night that I matched with Cale, I began a conversation with another boy, Richard.
This conversation was much different. I started off by telling him that I sometimes attempt to be a writer, but I was feeling unmotivated lately.
“Well soon you’ll be able to write about our perfect first date that leads to a whirlwind romance and ultimately culminates in me breaking your heart. So that’ll be fun,” he said.
Immediately I knew I had found someone special, or at least interesting, which is most important. We went on to discuss how we would make our first date terrible and who would ultimately be the one to ruin it. I kind of got the sense at some points that he wasn’t kidding, which made me even more interested in him. Either he was smooth enough to carry on a completely ridiculous conversation without missing a beat, or he was a sadist. I liked both options.
Richard grew up “in” LA (more like LA-adjacent) and was going to some design school learning to design cars. The fact that he was a “womb-to-tomb Angeleno” (his words) could definitely be used to my advantage. I had been in LA less than a week and my roommate was mostly working so I didn’t really have anyone to show me around. I was determined to not mess this one up in the hopes of at least getting a tour out of it.
As the Tinder conversation continued, he kept bringing up the date that we were eventually going to go on and subsequently ruin somehow. He was thrown when I told him I don’t drink coffee or eat sushi – respectfully so, since those are LA’s two favorite things, especially for a first date. The date conversation continued, seemingly as a joke. At this point I didn’t know if he actually wanted to go on a date with me or if we were going to continue this joke forever. We eventually made our way into picking a day and time for our “disaster date.”
I ended the conversation on Tinder as I normally do: a detailed description of a ritual sacrifice and my phone number. The date was set for Thursday of that week.
On Wednesday, if you recall, I spent the night with Cale. I liked Cale so much that I considered canceling with Richard for later that night. But then I remembered that if something seems too good to be true, it is, so I might as well keep my options open. I also really liked the possibility of the date with Richard going well and eventually dating two guys at once. Delusions like these are why I should wear an ID bracelet that says “don’t get your hopes up, Jack.”
After pestering me to pick a place for our date and getting nothing from me because I had literally lived in LA for 4 days, Richard planned for us to go to a rooftop bar in Downtown LA. I had him pick me up from my apartment because I was scared to drive and park downtown and also because I like feeling like a princess.
As my pickup time approached, I managed my time poorly, as usual. After I took a long shower while listening to Taylor Swift and dried and styled my hair, I had about ten minutes to pick out an outfit. I have a knack for just throwing outfits together, but it only works when the “I’m too cool to give a fuck if I’m underdressed” vibe is appropriate. Usually I think it is, mostly because I’m too cool to give a fuck, but this time it wasn’t. This was a first date and the place we were going sounded pretty fancy.
This was in early October, so the temperature in Southern California was a consistent 95 degrees; I texted Richard to ask if I could wear cut-off shorts and a tank-top, my go-to summer look. He basically said “um, maybe you should try to step it up a bit. Maybe we’ll go to a trailer park on our second date.”
So I found some shorts that were still inappropriately short (I wasn’t going to go off-brand just for some boy who’s taking me to a fancy rooftop bar), but not shredded or frayed and threw a button-up over my tank-top. I had just slid on a pair of white sneakers with a watercolor flow print when he texted saying he was outside my building.
Side note: why do boys not come to the door anymore? I live with a 25 year old struggling stand-up comedian, not my large bulking father with a collection of shotguns. Is picking your date up at the door really a part of the “chivalry” that everyone says is dead? Or do they not teach young boys to do that outside of the South? Maybe it’s an LA thing because finding a place to park for two minutes while you go ring the doorbell would add another 15 minutes to your travel time.
I took one last glance in the mirror before I headed out and really felt that something was off. I was wearing three different shades of blue and two clashing prints overtop of one another, but I really felt those were working for me. I figured it out as Richard sat outside waiting in his car: the addition of the collared button-up shirt made the whole look a little too preppy for me. And by “a little too preppy,” I mean only a little preppy, which is too much for me. It was too late to change the whole look and I almost cried when I realized I didn’t really have any other option. I only own tank-tops and he’d already shot that down, so my only option was the button-up.
Then it hit me: the shoes. I was and still am absolutely in love with the shoes, but they’ve never been very “me.” I ditched them and threw on my combat boots and I finally felt like myself again. I ran out the door hoping that I didn’t look too weird, but knew that it was better this way. He should know now.
I got into his tiny car and was sort of surprised when I got a look at him. It wasn’t that he didn’t look like his Tinder pictures, it was just that I had forgotten what his Tinder pictures looked like. I had been so obsessed with Cale for the past 18 hours that I couldn’t remember what any other boy looked like. Ultimately it was OK because he was cute.
Instead of making small talk in the car, he demanded that I tell him a secret. I’ve made it a policy to keep all my friends’ secrets but never hold any of my own, so that wasn’t going to be an easy task. Plus, who tells a secret on a first date? Me. I told him my one and only secret that no one – outside of the full bar of people who witnessed it happen – will ever know. When I become famous and he ultimately talks to tabloids about me, he better not tell them.
We got downtown and found a parking space and when he stepped out of the car, I was relieved to see that he was also wearing shorts and combat boots. His were Doc Martens and I got mine half-off at Rack Room and the laces have several knots in them where they’ve broken and I’ve tied them together, but basically we were on the same page.
When we made it to the roof of the Ace Hotel, he paid for our first round of drinks and we found some seats outside by the pool. (Yeah.)
I had to take a moment to look at the view of Downtown and the rest of LA, which I thought was a very normal thing to do for someone who just arrived. He didn’t quite get what I was doing, so I had to cut my viewing time short and refrain from walking to all the other sides of the building to take in all the views.
I did a lot of talking on this date, as I normally do, mostly about my best friend and all the things I adore about her. I got so used to her going on dates with me in college that I think I formed a subconscious need for her to be somewhat present on every date.
I also made a lot of jokes about how much I hate life and how I wished every day that a plane engine would crash into my house, killing me on impact. Over the past few years, I’ve managed to remove most of the emotion from my voice and face, so the more I joked, the more I probably seemed serious. I could tell with every passing minute that what I was doing was wrong and he was probably going to end the date early and just pass me off to a police officer on the street to either take me home or to a mental hospital.
I managed to make it until about midnight before he needed to leave. When we got back to his car, it really hit me again how awful I was and I overcompensated by asking every small-talk question I could think of on the ride home. He hugged me when I got out of the car at my apartment; there was no attempt at a kiss or mention of a second date.
Knowing that I had ruined that date didn’t bother me too much. At this point I had no idea Cale was going to ghost on me so soon, especially after we’d made semi-concrete plans to see each other again, so I had my obsession with him on the backburner to get me through the pain of a ruined date.
Also, Richard and I had promised each other a disastrous date, so basically I delivered.
The next night I got drunk and went out with my roommate and, of course, texted Cale. At some point early in the night he told me he was going to bed, but I needed attention so I texted Richard. I found a funny picture that said “I avoca-don’t want to be alive” online while I was in line for the bathroom, so I sent it to him hoping that it would break the ice. Or at least confirm that I had been joking when I talked about dying for four hours straight.
To my surprise, he responded. It was something normal and not along the lines of “please never contact me again,” so I was feeling good. Before I blacked out, he made a comment about how attractive he thought I was and I was baffled because I genuinely thought he wasn’t interested. I was too drunk to play it cool, so I told him I was baffled. Another good move.
The next day, I realized that I had texted him one more time post-blackout, something that made absolutely no sense. I texted him to apologize and it led to a nice conversation. Maybe I will get to juggle two boys at once, I thought. I should never listen to myself. Don’t get your hopes up, Jack.
The next day, Cale stopped responding to my texts. For a while I kind of hoped that he was hospitalized for being attacked by a Hillary Clinton supporter and was going to text me in a week once he’d been discharged. That didn’t happen, so I wasn’t juggling two guys. But on the plus side, I did get to juggle Richard (he’s a handful).
School kept Richard pretty busy, so I didn’t see him much. We texted every day, though, which is good enough for me. I didn’t realize I could simultaneously get attention and be alone in my bedroom, but there was a way and this was it.
The second time I saw him was about two weeks later, on Halloween. I met up with him and a few of his friends on Santa Monica and we had a grand time. I don’t know when I managed to get as drunk as I was, since I hadn’t had time to drink all that much, but my memory of being with his friends is only about 20% there. Once my roommate finally made it out, I arranged for him to come meet me and Richard wherever it was that we were standing. Richard’s friends decided to leave, but he stayed with me, which is a lot sweeter than I realized in that moment.
In the few minutes between his friends leaving and my roommate arriving, I did something that I’m almost too embarrassed to write. Something I’ve never done and never plan to do again. We had been inching closer and closer to each other in the few hours that we were together, but the moment never really came, so I decided to make the moment while I had a chance.
“Hey…” I interrupted him. “Can I kiss you?”
Luckily he did not laugh in my face; he just nodded and puckered up for the shortest kiss of my life. I felt like an idiot. He told me the next day that he thought it was cute and that he immediately texted his friend about it when I wasn’t paying attention. That still doesn’t make me feel much better about it.
Richard and I made our way to a bar with my roommate and his boyfriend du jour and ended up making out and dancing all night with what I thought was a group of strangers*. Over the course of the night, my roommate nearly got into a fight with one of these strangers and I tried to convince Richard to steal something from them. I found out about a week later that they were not strangers, but actually good friends of Richards, which is why he wouldn’t steal from them.
*We only danced with the strangers, not made out with them.
After being at the bar for about half an hour, we stopped dancing for a minute and were approached by a lesbian couple. “Are you two dating?” one of them asked.
It’s very rare that I’m speechless, but I honestly had no idea what to say in that moment. The sane answer was “no, not exactly” or something vague like that. I looked at Richard to see if he was as confused as I was, but he wasn’t.
Apparently we were dating.
Once we left the bar, I walked hand-in-hand with Richard for about 4 miles until we reached his car elsewhere in West Hollywood and he drove me home.
Over the next week or so, we continued to text, but the mood changed. He was snarky more often than he was flirty and sometimes it seemed inconvenient for me to be talking to him. Almost everything I said to him was made into a joke, or he would just find a way to poke fun at me. I convinced myself for a while that it was just his sense of humor and that he really was flirting, but it got old fast.
I never really analyzed my feelings for him to see if putting up with his bratty-ness was worth it, and I just continued to go along with it. I had someone paying me some attention, after all, even if it was forced and occasionally just mean.
About a week after Halloween, we found a time to hang out and he took me to In N Out Burger, which I pretended to like because it seems like life in LA depends on it. I mean, it was fine, but clearly no one from LA has ever been to the East Coast, home of Cook Out. But Richard swore In N Out was then end-all-be-all of fast food, mostly because it was LA-based. Actually, he was absolutely obsessed with LA in all aspects. On our first date and in the weeks after, I talked about all the places I wanted to see and live in the future and he scoffed at every one of them. “It’s just not LA,” he would say.
That date was awkward – a lot of forced conversation that was almost entirely prompted by me. He apologized, saying that he was just tired from a long week at school and I believed him. I told myself that if he really didn’t want to be doing this anymore, he wouldn’t have agreed to see me again.
So that thought held me over for the next week or so of snarky texts from him. Turns out I was right for once, because once he decided he didn’t want to be doing it anymore, I didn’t see him again.
It was a Friday and we were in the middle of a completely normal text conversation; actually it was slightly abnormal because it was relatively light-hearted compared to the conversations we’d shared in the weeks prior. I asked him if he wanted to hang out that Sunday because I had the day off. No response. I’m guessing I just wasn’t LA enough.
To me, there’s nothing more despicable when it comes to dating than just ignoring a person instead of actually ending things. But I’ve learned over the past few years that it’s easiest to just let people go when they want to be let go. Almost every fiber of my being wanted to text him and tell him what a bratty jerk he was, but I knew that wouldn’t solve anything. It would probably even make him feel a little better about himself.
So I was doing pretty well pretending I was over him and unaffected by his general assholery, but then I came across an opportunity that I couldn’t pass up. I had been reading Anna Kendrick’s memoir, “Scrappy Little Nobody,” which focuses a lot on how difficult it is to live and date in LA. She provided me with the perfect “final” thing to say to Richard, so my last text to him is this:
I felt it was the least crazy thing to pull out of my basket of crazy things that I keep on hand for boys who reject me. As expected, he never responded.