Love don't cost a thing - or does it?

On dating in my thirties

Hey suckers!

I’m not exactly sure how four months went by so fast without writing on here. It feels like I blinked and suddenly it was June. But in that timespan, I feel like I’ve become a different person. The past few years have felt like a transition period during which I’ve been running endlessly, trying to find the light at the end of the tunnel. I feel like after the past few months I’m finally coming to the close of whatever this journey was supposed to amount to.

I write this from someone’s apartment, which is located in a place I had to catch a flight to get to. I promised myself back in 2020 that I would never again get on a plane to meet someone I didn’t know well — because the last trip I did like this ended horribly. But here I am. This time is different so far, although the memories of the past have sparked a short story in me that I plan to write sometime this week. But, for now, I shall muse on my recent thoughts on dating. Walk with me…

The pros and cons of having a lot of dating experience

Lately I’ve been thinking a lot about dating and how different it is as a 30-something woman with life experience compared to how risky it felt in my 20s. Even just four years ago, when shit hit the fan while I was in a different city with a man I had only met weeks prior, I didn’t know what to do or who to talk to. Now, I can spot the red flags from a mile away — or I’m able to talk to friends who can do the same. I also have the confidence (and resources) to speak up and act when things aren’t aligning with me.

For instance, a month ago I was dabbling with the idea of having a sugar daddy (for the plot) and went on a date with a much older man. All it took was for me to see his freshly inked tattoo sleeve and to hear his comments about only being attracted to much younger women to realize…no amount of money could cover the cost of dealing with the kind of baggage that was radiating off of him. It was impossible to ignore.

Kiah from a few years ago would have politely kept seeing him until he decided he didn’t want to be with me. By contrast, present Kiah had no problem telling him he was way too old for my preference. (I didn’t bring up the baggage thing to him because that was just an educated assumption that could totally be untrue.)

Would I have seen him again for the free food if he was still into it? In this economy?? Absolutely. Ya girl loves free food. But I wasn’t about to do that without him knowing I didn’t see it working out for us, even if he was willing to cover all my bills just to date me. He ended up ghosting me, which is fair because my last message to him just doubled down on the fact that I probably wouldn’t wrap my head around how old he was in looks and conversation. (Not to be ageist — aging is beautiful! I just don’t want to be with someone who is old enough to be my own father, no matter how many successful companies they have. And I’m not desperate enough for money to force it.)

At the same time, I’ve been having recent conversations with one of my very close male friends who struggles as a successful man dating in his thirties. Maybe “struggle” isn’t the right word, but from his perspective it’s hard to find “age appropriate” women who aren’t jaded or who aren’t more focused on what they can get from him.

To paraphrase some of our conversations on the topic, it’s like women around our age (late twenties/early thirties) are just waiting for him to mess up. They set up arbitrary “tests” or have expectations that they haven’t communicated to him. Then, they drop him for someone else on their roster because having a roster is just the norm for a lot of people these days.

I can sympathize with this. It’s got to be rough to invest your time, energy, and finances into someone who is already starting from the perspective that they don’t like you or that you’re not relationship material. Or, possibly worse, who is just dating you as a back up if the real person they want to be with doesn’t pan out.

Do I think dating 18 year olds is the answer to his problems? Probably not, especially if he’s looking for something serious long term. But it is undeniable, from my perspective, that dating someone who has had the time to tally up a greater share of negative experiences is going to be more of an uphill battle compared to the alternative. There’s a need for all of us to be careful about who we give our time and energy to, and that’s especially true if you’ve been burnt before.

The uncomfortable truth: money matters

Leticia Padua, known online as SheraSeven or Shera Seven, is an American livestreamer, YouTuber, dating coach, and social media personality. Her YouTube livestreams give dating advice to single women about marrying rich and getting money from men. (From Wikipedia.)

With the rise of social media accounts promoting hypergamy, like SheraSeven, I think a lot of women who are fed up with negative dating experiences are starting to date in ways that are more transactional in lieu of wanting to put effort into something that is less tied to what a partner can materially give them.

Now, to be honest, I’m not against hypergamy at all. Dating the wrong person who is not financially set up can really hold you back. Especially as a woman, where if you plan to have kids your earning potential over the course of your life is lesser by virtue of the fact that bringing a life into this world often requires time off from being able to work or being able to work at the same volume. (And this is aside from the gender-pay gap that exists between male- and female-dominated industries.)

Yes, I know this is taking a turn to what some may deem superficial. Even though it’s common to find these conversations online these days, it feels gross to talk about how important money is when you’re dating someone. Relationships are about more than that (hence why I quickly got over the sugar daddy idea lol). But, in the current era of late-stage capitalism, it’s not something I think can be ignored. And, oh boy, have I ignored it.

The last relationship I was in had me funnelling my resources into making things work when I wasn’t getting an equal amount in return. I was paying for hotels and AirBnBs to see each other and being let down when he decided to eat into that time by disappearing for hours to do his own thing. I was being guilt-tripped for expecting him to still make time for me when he started working again (fewer days than I was, I should add). I was expected to put my needs on the back burner to help him sort through issues that he should have been going to therapy for.

Hypergamy aside, if I had at least cared that the person I was with had a stable job and a plan forward in life that they were actually making efforts to execute in a reasonable amount of time, I would be in a very different place financially right now. When he finally did start working full time but he wasn’t nearly as giving as I had been, I got called transactional for being frustrated by that.

If I was really well off, maybe I could afford to care less. But I was out here trying to pay down my student loans, covering my own rent and bills while dating someone I once had to encourage to get a job and who’s idea of “the next step” was to have me move in with him at his parents’ house.

That’s not to shame anyone living at one’s parents’ home to save money. I was doing just that for the past year and I totally recommend it when possible in the short-term to save money. But when you’re trying to move forward in a relationship in your thirties, that can’t be the only plan in place without any aspirations for more.

Let’s be honest with ourselves

This could be us but you playing. 😒

Going back to my friend’s situation, I understand both sides. I’m out here on this trip actively staying positive and open-minded with this new person I’m spending time with because it would be unfair for me to project my past issues on someone who hasn’t had a chance to show me who they are. (Thankfully, it’s not been hard to do because so far he’s great.)

At the same time, I have also been the person that has gone too far in giving chances when it’s clear our futures aren’t aligned. That goes for people I’ve dated who have had money, and those I’ve dated who have not. You want to look out for signs that you may not be getting what you need.

There’s a fine line, and going too far in either direction can amount to self-sabotage. Whether you’re sabotaging something that could potentially be great, or sabotaging your own success waiting for someone to get their shit together so you can start to plan for the future.

I think the important thing is to know what you want to get out of your dating experiences. What do you need in a partner for you to be happy? What are your dealbreakers? What’s negotiable for you? And — although I know a lot of people are going to hate this — what are you bringing to the table?

At the end of a day, relationships are a two-way street. If there is not somewhat equal give and take on each side, resentment is going to build up.

If you’re focused on hypergamy, cool — there are plenty of partners you can find who will be open to that kind of dynamic. But, remember, your partner also deserves to have their needs met.

Now, if you are the one sacrificing your ideal to make it work for someone, you need to make sure you’re okay with those sacrifices in the grand scheme of things. Is this person giving you everything else you want? Or are you constantly dreaming of more?

Finally, it’s also important to avoid projecting your past on someone you barely know. Don’t be dumb and ignore the red flags, but don’t make something into a red flag if it doesn’t have to be. If you’ve got trust issues, it’s important to develop the self-awareness to realize if what you’re seeing is really the other person or if it’s your past experience warping what you’re seeing into something it’s not. The same goes for the opinions of your friends, who may be projecting their own assumptions onto what you’re experiencing.

Anyways, stay tuned for the short story I’m working on while I cross my fingers no one I’ve dated ever reads this.

Thanks for reading suck it and see. I’ll be back shortly with a new post — until then, be sure to subscribe to receive updates right in your inbox.