Episode 16 started with three stories going around online. A man asked his date to pay back $1,050 after a first date that went nowhere. A man left his date at a nail salon after she asked him to cover a $120 treatment. And a TikTok told men their dating problem is simple: they’re boring.
Neither of us has been on a first date in a long time, so we came at it as two guys looking back with what we know now. We didn’t agree on everything. We did land on five rules, and they work whether you’re 25 or getting back out there at 45.
Don’t spend more money on that first date than you’re willing to lose.
Rule 1: Set the number before you ask
This is Jose’s rule, and it’s the whole answer to the $1,050 guy. A first date only shows you the surface. Money can’t show you who someone is, what they bring to the table or how they treat people. So pick your number before you ask: the amount you’re fine never seeing again if it goes nowhere.
And forget the refund. As Jason put it, nobody promised that guy a good date or his money back. If you spend it, it’s spent. The only refund you control is spending less the first time.
Rule 2: If you invite, you pay
Jose runs this rule with everyone, not only dates. If he picks the place and makes the plan, he covers it, because the other person didn’t get a vote on the price. That holds within reason. Picking the restaurant doesn’t mean signing up for a $1,000 bottle of wine.
It cuts the other way too. If she invites you along to her plan, like a nail appointment, and hands you the bill, it’s fair to say that wasn’t the deal. And if she offers to split, Jason’s advice is simple: let her. Don’t fight it.
If I invite, I’m going to pay.
Rule 3: Invite her to something you already love
This is Jason’s favorite move. Skip the big dinner and invite her to something you’d do anyway: bowling and a couple of beers, an Astros game, a soccer match at a sports bar with a few friends, your favorite taco spot.
Three things happen. You have a good time even if there’s no spark. She sees you excited about something real, which is a lot easier than faking excitement about a fancy menu. And if she’s not into it, she’ll say no or suggest something else. Either way, you learn something before you’ve spent much.
Rule 4: Start with tacos, build to the steakhouse
You don’t need to open with the priciest place in town. Start where you actually eat. If things are going well, take her somewhere nicer you save for special nights, and tell her that’s what it is.
Watch the precedent you set. If the first date is a $120 bill you didn’t plan for, that becomes the baseline. Jose pushed back on this one: some people will write you off for a taco truck. Fair. That tells you something too.
If you’re single, there’s no second paycheck covering the night out. Give dating its own line in the budget, like groceries or gas. At $200 to $300 a dinner, five dates is $1,000 to $1,500, so it adds up fast. If the money isn’t there this month, Jose’s advice was blunt: stay home this month and come back to it.
Rule 5: Ask more questions than you answer
The TikTok said men are boring. The number one complaint Jason has heard from people coming home from a bad date is more specific: he only talked about himself.
The fix is to ask. And if she brings up something you know nothing about, that’s not a problem. Nobody expects you to be an expert in her job. Jose once ended up deep in a conversation about nuclear reactor parts with an engineer at a birthday party, and she said most people stop talking the moment it comes up. You don’t need his trivia. You need follow-up questions.
What do you actually do day to day? What got you into that? Has it taken you anywhere good? What’s the best thing you ate there? What are you into when you’re not working? Then listen, and ask one more about the answer.
One more thing: put the phone away. If you can look something up in two seconds, it’s tempting to stop asking people. Ask the person instead.
If you can be interested, you’ll have an opportunity to be interesting.
Your turn
Who should pay on a first date: whoever asked, the man, or split it down the middle? Tell us where you land. We’ll read every answer.