Dating In Your 30s: Ugh

How I feel about dating

A friend of mine was telling me about the two years he spent online dating in San Francisco. He went on hundreds of dates, which is the actual definition of Hell for me. He’s very outgoing and has tons of energy (he checks into Soul Cycle at 6am every day according to his Facebook page) so this wasn’t at all surprising to me, but just hearing the phrase “online dating” gives me exhaustion.

Of all the stories he told me, I specifically remember one about a time he hooked up with a woman and heard faint cello music outside her bedroom door. The woman apparently enlisted her roommate to play the cello while they “made love.” I can’t tell if that’s extremely romantic or the dumbest thing I’ve ever heard. This woman also coined the term “tomato season” to describe being on her period. He’s 36 and still hasn’t met his wife, but at least I can now forever make fun of him by dropping “tomato season” casually in our text conversations.

Something strange happens when you’re a woman and you become single in your thirties: Sure, you google egg-freezing and get uncontrollably emotional at videos of laughing babies which make your ovaries scream silently to your brain “YOU NEED ONE OF THESE IMMEDIATELY,” but more importantly every person you go out with is no longer just a “date.” They become a potential husband or wife. Instead of wondering if you could stand this person for a few years, you wonder if you could stand them for the rest of your entire fucking life. When you really think about it, dating is just a slow progression of finding out all the terrible stuff about someone and deciding if you can live with it or not.

Up until a few months ago, I wasn’t sure if I wanted to have children. Actually, I’ve always been sure that I most likely wanted children, but I wasn’t ready to admit that until recently. I didn’t want to scare off potential boyfriends, which now sounds very immature and ridiculous. I’ve dated men in their forties who were still unsure about children and marriage, but I also think they were just saying “I might have children someday” to appease potential younger girlfriends. Well played, older men.

While on dates with three different guys in the past few months, I’ve given three different answers when asked if I wanted children: The first to a guy who was way too cool for me: “Ehh, haven’t really thought about it.” The next to a guy I wasn’t really into, so I felt I could be completely honest: “Yeah, definitely.” And the third was, “Probably, I think?” I have no reason to alter my answer based on who I’m talking to, but that feeling of wanting to be perfect for someone is a powerful thing.

The weirdest/best/worst part of dating in LA is the guys on dating apps from bands that headlined Lollapalooza in the mid 90s. My reaction always goes from “Holy shit! The singer from a certain counting birds band!” to “He’s 48 now and on a dating app? Huh.” But, out of curiosity, I swipe right and immediately match with all of them. The chances of being in a romantic relationship with a guitarist from the Butthole Surfers is very low, so I have no other choice but to exchange messages only using song titles and lyrics from their music:

“I’m actually from Nashville, I came here with a suitcase in my hand, really trying to meet a boy who looks just like Elvis.”

“Lets drive up to Hillside Manor sometime after 2am and talk a little while about the year.”

“It’s been a long December, I mean April, but this year will totes be better than the last.”

To which he responds: “lol.” Not even LOL. He was too busy responding to the plethora of pussy that he couldn’t even use uppercase letters. Totally understandable.

Another guy from a band asked me to go bowling before we even exchanged a single message. What if I was a nightmare? Or a murderer? His standards must be so low that I couldn’t warrant meeting him. At least ask me how I’m doing? I politely declined and said, “Enjoy a Heine from a crowded ice box for me.”

Dating apps are just devices to make yourself seem like the most fun person in the world. I play basketball! I’ve been to Copenhagen! I threw a tomahawk once! The whole idea is to persuade others to think you’re so engrossed in amazing things that you don’t have time for anything mediocre. We all want someone to feel like they just matched with the most wonderful, smart, and intriguing human being alive. I’d love be known as Melissa “her life looks fucking sweet” Stetten, but of course, in reality, I spend a lot of time binge watching TV shows, comparing myself to hot models on Instagram, and looking at before and after photos of lip injections. No one has to know that, though, especially not a potential boyfriend.

Initial text conversations with new people invariably start out as everything being “great!” “amazing!” “wonderful!” even if it’s not. I’m guilty of this, as are most people. I’ve never quite figured out why this happens, maybe because we’re all looking for an extremely happy person to spend the rest of our lives with? Sure, that’d be nice. And if everything is great, amazing, and wonderful: fuck you, you’re lying (but seriously what dose of Lexapro are you taking because 20mg is kinda too much but 5mg might not be enough?)

Another stereotypical guy found on dating apps in LA are actors. So. Many. Actors. I swipe left on headshots faster than I do “entrepreneurs” with Burning Man selfies. I have a lot of amazing friends who are actors, but every relationship I’ve had with an actor has ended with me secretly smiling when their new movie gets below 60% on Rotten Tomatoes. So, obviously, when I saw an actor from one of my favorite shows on a dating app I pressed the “no thanks” button.


I knew it was going to be a disaster. I knew it would never work out, but yet here I was, letting my inquiring mind take over, and it was an immediate match. Ugh. Great. What do I do now? Say something clever and funny? Oh great, he said something first, I guess I’ll respond. Hah, that was actually funny. Maybe he’s not terrible? He wants to get coffee with me and not an alcoholic beverage? Wow, that’s what people do when they actually want to get to know you. Tomorrow? Yeah, I could do tomorrow. HERE WE GO.

A few weeks later: Am I dating this person? How do you tell? Does hanging out six times in two weeks mean dating? He tells me he will be in NYC next week and I casually text “yeah ill be in NYC next week too,” like my life is so fabulous I’m constantly taking random trips to New York. In actuality I haven’t been to New York in over a year and I’ve already picked out my outfits and made a list of restaurants I want to eat at. I’ve basically put together an entire vision board for this trip, but yeah, he doesn’t need to know that.

In New York he texts “you should come by the set today.” I want to go, but I didn’t because I wanted to seem like I had too many important things to do besides visit him on the set of one of my favorite TV shows. Great reasoning, ya dingbat. Instead, I invite him to a bar that night, and he comes, and I have to stand awkwardly next to him as girls take selfies with him. I wonder if they’re thinking, “Is that his girlfriend? She must be so cool!” while I’m standing there with a huge fake smile, sipping my empty beer, thinking about how he doesn’t really like Radiohead or 90s RnB (he’s a monster), knowing this will never work, and really wanting to be back at the AirBnb in Brooklyn with my friends eating pizza. But I’m there. In the East Village. Trying to figure out if he’s actually charming and good looking, or if it’s all a facade because that’s what he plays on TV.

Back in LA, he came over to my house after we walked around the neighborhood one night smelling flowers (I don’t know either). I had just moved into a new apartment so boxes and clothes were everywhere. I didn’t have time to put away my “If I Did It: The OJ Simpson Story” book or the random cat toys laying around, so I had no other choice but to completely own that this was my life. I didn’t even have a bed frame yet (I was staining it in my garage, THANK YOU), but I was hoping he would find it endearing at the least.

My “makeout” playlist hadn’t been updated in over a year, but I had to put on some sort of noise because sitting in silence at this point in our relationship only invited more uneasiness. Things were going fine, until a song started playing that I realized was used in an episode of his show. Great. Did he notice? Does he think I’m only hanging out with him because he’s on that show? Am I hanging out with him just because he’s on TV? Would I find him attractive and interesting if I had just randomly met him somewhere? Do we even have anything in common? Why did he just tell me he hasn’t washed his hair with shampoo in 10 years? Why do I feel so uncomfortable around him? I think I’m hungry.

The next day my friend texted me, “Are you going to _____’s tonight?

“No, what’s happening there?”

“He invited me to a party on Facebook a few days ago”

“Weird, he didn’t say anything to me last night WHEN WE WERE MAKING OUT”

“That’s very strange. Come with me I guess?”

“I can’t show up uninvited, that’s just awful and even too weird for me”

I sat in my garage, surrounded by wood and sand paper, listening to Beyonce, thinking of the many texts I could, or could not, send: “Hey man, you invited my friend to your party, she’s only met you once and was kinda confused cuz she knows we’ve been talking, but you seem like a super social dude so that’s cool I guess. Anyway. What the fuck?” I ultimately settled on this one: “My friend is going to your party tonight, small world!”

His response: “Oh cool, you should come.”

NOOOO! No I shouldn’t! NO WAY! You didn’t invite me and now this is weird!

I replied: “Can’t, but have fun!”

We exchanged a few more texts after that, but it was too weird now. It was time to wave the white flag.

“Maybe he thinks of you as like a girlfriend type and isn’t ready for you to meet his friends yet?” Said my very optimistic friend.

I wasn’t sure how to feel. Sad? We had only been dating for a month, was I allowed to be sad? I was definitely annoyed and confused. But the most overwhelming emotion I felt was disappointment. Not being invited to a party was the least of my worries. It was realizing at that moment I had to start over.

A new guy.

A new person to tell your life story to.

Another first date.

Another attempt at connecting.

Another person who may or may not like Radiohead as much as I do.

Another reason to worry about if someone likes you as much as you like them.

Having to tell someone you don’t like them as much as they like you.

More sadness.

More excitement.

More disappointment.


In the end, we’re all just trying to find someone we love (and who loves us) just as much as cats love empty boxes.

But holy fuck, dating is exhausting.

15 thoughts on “Dating In Your 30s: Ugh”

  1. I got to a point where I gave everyone 1 date. Yes, even the guy who was talking about how his baby’s mama stabbed him. I figured that after 30, we can take all we have learned and not waste energy trying to make a relationship out of something not right in the first 15 minutes. If you have to try so hard to make something work at the beginning, you will never get through the real stuff. I eventually met my husband while sitting at a bar, trying to avoid making eye contact with anyone, so I wouldn’t have to talk to them. Dating is painful and tiring, but it’s better than losing hope. So until you find the one, think of this all as a comedy of errors and laugh, it is better than crying.

  2. Ugh, that sucks. It feels so dry to admit what you want from someone, yet it’s integral to the relationship. Then get labeled as “clingy” or “needy” because how dare openness enter the relationship.

  3. Thank you for writing such lovely essay. And even though I’m no expert on love, my advice to you… Give coah Vanger a chance!

  4. Ha! I really enjoyed reading this. “Tomato Season”, I don’t think I’ll ever be able to erase that one. I listened to the final Bachelorette podcast and I’m excited for your web series!

  5. So I have a followup to your dating story…I once went on a date that I thought was going pretty well, then we went back to her place. We sat on the couch and I looked up. No cellos, but hundreds of shelves with dragons. I liked the girl but the idea of kissing under dragon watch was a little much. Anyway, many stories….thanks for sharing yours. @gr8fullyfeclub and smart phone frugal

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