Dating In Your 30s: Ugh

How I feel about dating

A friend of mine was telling me about the two years he spent dating in San Francisco. He went on hundreds of dates, yes HUNDREDS, which is the actual definition of Hell for me. He’s very outgoing and has tons of energy- he’s one of those Soul Cycle freaks- so this lifestyle suited him well.

Of all the stories he told me, I specifically remember one about a time he hooked up with a woman and heard feint 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 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 THOSE IMMEDIATELY,” but more importantly every person you meet 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. 

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. I’ve dated men in their forties who were still unsure about children, but I also think they were just saying “I might have children someday” to appease potential younger girlfriends.  

While on dates with three different guys in the past few months, I’ve given three different answers when asked if I wanted children: “Ehh, haven’t really thought about it,” and “Yeah, definitely,” and “Probably, I think?”

The saddest/best/worst part of dating in LA is the guys on Raya from bands that were popular when I was in high school. My reaction always goes from “Holy shit! The singer from Counting Crows!” to “He’s 48 now and on a dating app? Eww?”  But, out of curiosity, I swipe right and immediately match with all of them. I have no other choice but to exchange messages only using song titles and lyrics from their music.

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

“It’s been a VERY long December.”

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 I was obsessed with in high school asked me to go bowling before we even exchanged a single message. What if I was a nightmare? 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 lame. 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.

Another 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. JK.

I knew it was going to be a disaster. I knew it would never work out, but yet here I was, letting my curiosity 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.

Fast forward 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 the documentary of my basketball team is premiering at Tribeca Film fest and I haven’t been to New York in over a year.  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.  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, 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, that’s what he wanted to do). 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 was not an option yet. 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 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. 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 clearly over.

“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.

Sigh.

Holy fuck, dating is exhausting.

17 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

  6. Dating these days really sucks. I hope you have found that someone special by now since this was 3 years ago. I found the women were always playing some sort of game. I found the best people to meet were from the activities I did.

    BTW your Lincoln commercial is fantastic!

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