Last week a finance guy from Hinge invited me on a date, and I accepted. He pulled up in a silver Mercedes. We went to an Italian place for wine and tiramisu, and he paid with his black Amex. The next morning, I got a Venmo request for $49.37 with a note: “Dinner—your half.” As a woman, I think the man should pay for the first date. Should I pay him for my share, or just ghost him?
VENMO VEXED
Hold on, Vexed. He handed over a black Amex like a boss, then Venmo-ed you like roommates sharing Papa John’s? Cheap move.
Pay him back with a check—a reality check.
Venmo him exactly $0.02, and add this note: “Here’s my two cents: The person who does the inviting should pay, especially when they drive a Mercedes. Good luck!”
Sure, you could just ghost him, but silence teaches him nothing. A witty, astute reply might make him more generous—and save the next woman from an itemized tiramisu.
He needs to understand that how you handle money around your date reveals character. A generous gesture (even a modest one) signals thoughtfulness. A nickel-and-dime move signals insecurity and scarcity.
If you take someone to a nice Italian spot, then Venmo-request them the next morning, that’s not “modern” or “equitable.” It’s cheap and passive-aggressive.
Here’s the rule I give all my coaching clients: The person who initiates the date should pay. Period. It’s not about gender—it’s about effort, generosity, and showing that you value getting to know someone.
So send your two cents and let him learn the real lesson—that romance should never come with a calculator.
And never date a man who doesn’t round down from $49.37. Yeesh. He probably expenses Tic Tacs.
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RHYME AND PUNISHMENT
I went on a first date last week with a woman from Bumble! I brought her a dozen red roses, told her she’s beautiful, and the next day I texted her a romantic poem about how wonderful she is. But she’s gone quiet. I thought women wanted a romantic guy who shows effort. What did I do wrong?
TRY HARD IN TOLEDO
Grand gestures like poems and roses might work in rom-coms, but in real life they make a guy seem needy at best and creepy at worst.
And believe me, I speak from experience. I’ve made all the mistakes a guy can make, including coming off as desperate. I once flew 3,000 miles to surprise a woman I’d never met, showing up on her doorstep with the gifts of flowers, Victoria’s Secret lingerie, and—I cringe as I type these words—a dildo mold kit in the shape of my manhood.
Yes, back in the day, I was quite the catch.
Here’s what happened. I was lonely, had watched too many rom-coms. In the movies, grand gestures get you the girl. In real life, they get you 60 to 90 days in county.
Vanessa lived in San Francisco. I lived in New York. We’d never met in person, but we had an online texting “relationship.” And she once mentioned that using a DIY dildo mold kit “could be fun someday.” So I did what any cool, confident, totally chill guy who hadn’t had a date in 27 months would do: I flew across the country to surprise her with a mold of my member.
I imagine the TSA agent staring at the X-ray and thinking, “This isn’t romance—it’s evidence.”
I dropped everything on her doorstep, then waited in my hotel for the excited call. I was ready for the sexathon weekend, the torrid romance. I waited. And waited.
Two days. Radio silence. I never heard from her again, and rightfully so.
In my mind, I was Lloyd Dobler from “Say Anything.” (Just replace the boombox with a dildo.) She thought I was Joe from “You.”
Try Hard, women like when a man makes his intentions clear. They don’t like when he seems ready to propose after two vodka-sodas and some calamari. That reads as desperation.
After a good first date, be vulnerable. Say, “I had a great time, and I’d love to see you again.” That’s clear, confident and enough.
Big gestures don’t read as romantic—they read as desperate. They say, “I must win you over because I’m not enough.”
But you are enough! Real confidence isn’t about doing more. It’s about being authentic and knowing your worth.
Wait until you’re truly falling for each other to give gifts. Not date 1. More like date 21.
You like poems, so let me put it to you in verse form.
“No more roses, leave rhymes to the Bard/
Lest girls ghost you for trying too hard/
That’s my advice, the thing you should know/
Take it from the dude who gifted a dildo”
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GO WITH THE FLOWCHART
A woman told me she wants a guy who’s “spontaneous.” But I’m a big planner—I make itineraries for vacations, and plan meals a week in advance, and on dates I always have topics ready to talk about. How do I become more spontaneous on dates?
MAN WITH A PLAN
Easy. Just schedule spontaneity for the first and third Thursdays of the month, from 7:17 to 8:53 p.m.
