The first six dates
What to look for, what to skip, what to ask, when to pay, what kind of date to plan.
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§ Journey
What to look for, what to skip, what to ask, when to pay, what kind of date to plan.
The first time I went on six dates with one person after my divorce, I learned more about her on date five than dates one through four put together. The first three dates are largely an audition. The next three are when the real conversation begins, if there's one to be had.
Date one is can-we-have-a-conversation. That's it.
Date two is is-there-a-second-look. Most attraction at 40+ is built across dates two and three, not date one. Don't write off a date who didn't blow you away on Tuesday. Do write off the one who texted three times during the meal.
Date three is can-we-build-on-this. The question is whether the conversation has somewhere to go.
If you've done three dates and you still don't know whether to do four, that's an answer. It's a no, gently. Stop.
1. How she treats waiters, baristas, bouncers. This is the single highest-signal data point on a first date and most men ignore it. The real version of someone is the version you see when she's dealing with someone who can't help her.
2. Whether she asks questions back. The conversation moves both ways or it doesn't.
3. Alignment of values, not interests. You don't need to both love camping. You need to both think similar things matter.
4. Whether you laugh easily together. Six months in, you'll spend more time together being amused than being impressed.
5. How you feel the morning after. Not whether you're thinking about her. Whether you woke up lighter than the day before, or heavier.
Trying to impress. Don't pick the expensive restaurant on date one. The version of you in jeans, sober, on a Tuesday is the version she's potentially dating for the next decade.
The over-share at date three. By date three, share that hard things happened. Don't hand her the whole archive.
The "where is this going" conversation at date four. Date four is too early. Six dates and three weekends in, sure.
The phone, on the table. It isn't on the table. It isn't in your hand.
The drinking. One drink, maybe two. Not three, not four.
Throughout: don't over-text between dates. Once a day, warm, brief.
If by date three you're forcing the next one into the diary, stop:
"I've really enjoyed meeting you. I don't think there's quite the spark I'd want to keep going. I'd rather be straight with you than waste either of our time."
In a text, before she's in the Uber.
If she sends you that one, take it well. The clean exit is the one she'll remember kindly.
Six dates. Three for the audition. Three for the conversation. Pay attention. Be present. Trust the morning.
A blunt field guide to the first month after the conversation. Sleep, paperwork, the kids, and the part nobody warns you about.
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4 minWhen she ends it and you didn't see it coming. The first 72 hours, the stories you'll tell yourself, and what to actually do.
4 minA self-interrogation guide for the man considering ending his marriage. Not advice. Questions. The hard ones, in order.
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