There's a phase a lot of guys go through in their late 20s and early 30s where they think the way to be attractive is to spend money. I was deep in this phase for about three years. Let me tell you how badly it worked.

I was taking first dates to $80-a-plate restaurants. I was buying wine I couldn't tell apart from cheaper wine. I was always quietly insisting on paying. I thought I was being generous. I was actually being weird.

The dates were bad. The women were uncomfortable. Almost none of them turned into second dates. I thought I was just dating the wrong people. I was actually doing the wrong things.

What I was actually communicating

It took me a while to realize that taking a stranger to an $80 restaurant on a first date doesn't communicate "I am generous and successful." It communicates "I am trying to impress you, please be impressed."

Women aren't dumb. They can read the energy. The expensive dinner reads as a transaction. She's expected to be wowed by the venue, charmed by my wallet, and on some level she's expected to repay this somehow — with affection, with sex, with at least the appearance of being into it.

It's not that women are gold diggers. It's that the over-the-top first date creates a dynamic where she's essentially the audience to my performance, instead of two people getting to know each other. Nobody wants to be an audience on a first date.

The friend who set me straight

A female friend of mine in her late 30s asked me, after a particularly bad week of expensive failures, what I was actually trying to accomplish on these dates.

I said something like "I'm trying to show her I'm a high-quality guy who can take care of her."

She said, and I'll paraphrase because the actual quote was savage: nobody is asking you to take care of her on a first date. She's trying to figure out if she likes you. If she likes you, she'll figure out the rest later. The expensive dinner doesn't help her figure out if she likes you. It usually makes it harder.

What I switched to

First dates: a coffee or a single drink. Somewhere I actually like. Casual. Low-stakes. Easy to leave if it's not clicking. Easy to extend if it is.

Second dates if the first went well: something a little more interesting, but still casual. A walk somewhere, a museum, a hole-in-the-wall restaurant I love.

Third dates and beyond: now we can do the nicer thing. By date three, the expensive dinner reads as celebration instead of audition. The vibe is completely different because there's actual context.

The flip side: real generosity

Here's the thing though. There's a difference between trying to impress with money and being genuinely generous. The first one is performative. The second one is attractive.

Real generosity looks like: tipping well even when no one's watching. Not making a thing about who pays the bill. Picking up a coffee for her if you happened to be at the place. Remembering she mentioned she likes a specific thing and bringing it next time. Being kind to the server. Being kind to the bartender. Being kind to the person who bumped into you.

These things don't cost much money. They show character. Women notice all of them. They especially notice how you treat people you don't have to be nice to.

The bill question

I've thought a lot about the bill question. Here's where I've landed.

First date: I pay. Quietly, without fanfare. If she insists on splitting, I let her, but I never initiate that conversation. I don't make her feel weird about it either way.

Second date and onwards: it can vary. Sometimes she pays, sometimes I pay, sometimes we split. The energy is collaborative now. We're a thing. Not a guy trying to win a girl.

If we're going to be in any kind of ongoing thing, paying for everything every time is also weird. It maintains the audition vibe. Take turns. Trust her to want to participate in the relationship.

The platform helps

One thing I noticed when I switched most of my dating to DatingAbove — the women on there are almost always proposing things that are mutual. Coffee, drinks, a walk. They're not testing me with venue suggestions. The whole platform's vibe is built around real connection rather than the transactional thing the swipe apps accidentally encourage.

It removed a lot of the bill-anxiety because the dates themselves were structured to be casual. Made it much easier to just be a normal person on a date instead of a man trying to prove his worth via a wine list.

What actually attracts women

I want to end with this because I think a lot of guys get it backwards. Women are not attracted to how much money you spend on them. Women are attracted to men who feel comfortable in themselves, who treat people well, who are present, who are interested in them as people.

All of those things are free. They're also harder than dropping $200 on a tasting menu, which is why most guys default to the tasting menu.

Save your money. Be present instead. The dates will get better.