Eight Things I’ve Learned While Dating at 28

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1. Shit be changing all the time — and by shit I mean my sexual preferences

It’s 2023, gender and sexuality are on a spectrum, and apparently I’m sexually attracted to cis men, so that’s cool. I spent most of my early twenties worried about what label best reflected me and — don’t get me wrong — that kind of self-discovery was needed. As I approach 30, I wake up everyday a lot less concerned about who I’m seeing and much more interested in how I might surprise myself. Being fluidly queer is liberating, and it makes me so thankful I’m on the backend of my twenties.

2. I’ve noticed extremely specific patterns that are neither good nor bad, just oddly specific?

All of the past few people I’ve been on dates with cannot drive. They literally don’t have a driver’s license. My first serious girlfriend also couldn’t drive nor had a license. I’ve also almost exclusively dated people who are extremely into DnD, despite never having played it myself — or even having any interest in it. I guess I might say that I’m into nerds but the funny thing is, I’m not into any of the nerdy stuff that makes them nerds. Somehow, I always seem to find that golden retriever gamer who has ADHD.

3. Breakup texts are almost a weekly thing

Even though I really don’t date a lot of people at once, it always feels like I’m sending — or contemplating sending — a “let’s just be friends” text. For some people, this isn’t anything to get caught up on but, as a nonconfrontational, indecisive people-pleaser, it takes weeks of building myself up to communicate such a simple thing. This is what makes dating so exhausting. However, the older I get, the less personal these interactions become.

4. Do I want a hot girl summer or a spouse? Why can’t I have both?

…which is exactly why I end up in weird situationships. Every summer, the same thing happens. I want a cute summer fling (or flings) with the guarantee that come fall I’ll have someone for cuffing season. It doesn’t work like that, and it never has (at least for me). This summer in particular, I feel the pressure of meeting someone and settling down, but I also want that summertime lazy August affair. A perfect romance would exist in both worlds, but in this bleak dating scene, it seems like that reality is worlds away.

5. Suddenly my ovaries are working, and I quite literally feel the pressure

I’m a big wedding and traditions person, and all of my friends and family are either married, engaged, have children, or are in very serious long-term partnerships. This never used to bother me until I realized that in two to five years when I (hopefully) have a serious partner, all my friends will have whole families and won’t be as available to do all the fun wedding things I do for them now. Sure, life isn’t all about the “fun” young stuff, but I’ve dreamed of doing the whole wedding thing since I was a little girl: the rowdy bachelorette party, the cute family bridal shower, the bridal party with all my best friends fussing over me. It’s not so much that all my friends are having kids and I have baby fever; it’s more like I don’t want to get left in the dust to be runner-up in all my friends’ lives with no ride-or-die to rely on.

6. “Do you have a Snap?”

LITERALLY NO. Okay, I do, and I only got it because some younger cis straight man told me it’s his only method of communication. Is this what the kids are doing now (and to be clear, kids meaning Genz Z folks in their twenties)? Does this make me old? I had a whole DTR conversation via Snap last night, and I regret it. Then again, I also used it for adult fun last night, so how judgemental can I really be?

7. Things got a lot easier when I applied a vetting process

Up until about two years ago, I spent most of my romantic life convincing other people to be with me. It’s not that they didn’t like me; it’s more that I had a habit of cornering people into a traditional relationship despite the signs it probably should’ve just been a flirtationship or sex thing. Once I started seriously applying my checklist of green and red flags to folks I started seeing, the whole breakup text thing got a lot easier. It’s not personal; it’s just not what I’m looking for.

8. The absolute key to dating is having ride-or-die friends

I could not have taken on the past year of dating without my best friends. They’ve been there to pick out my outfits, help me craft that “wanna go out?” text, help me discern someone’s semi-shady intentions, answer embarrassing sex-related health questions, and even give me pointers and techniques for, you know, stuff. Even when the rollercoaster of dating dips down and has me ending the evening in tears, my best friends are always there to pick up the pieces, validate my feelings, and call people out on their shit when warranted. I couldn’t navigate my own boundaries, attachment styles, and hesitations without the consistent support of my girls.

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Em Win

Originally from Toledo, Ohio, Em now lives in Los Angeles where she does many odd jobs in addition to writing. When she's not sending 7-minute voice messages to friends and family, she enjoys swimming, yoga, candle-making, tarot, drag, and talking about the Enneagram.

Em has written 70 articles for us.


  1. Having a DTR conversation on Snapchat…I wouldn’t wish that on my worst enemy… Sending you more positive energy, I met my person on a dating app so I promise it can happen!

  2. This made me feel Seen…I’m also 28 right now. Dating feels like a hell cesspool. (Made in no way easier by having feelings for someone I cannot date because they are off-limits). #2 and #4 are particularly relatable!!! My weird pattern is I keep choosing people who drive large white murder vans to live their nomadic-ass #vanlives

  3. Needed this… I’ve been trying to get back into dating after being single for years at 26, and it’s tricky especially as someone with social awkwardness and anxiety.

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