Dating again, when you're ready

Eleven months after the separation, a friend asked me when I was going to "get back out there". I lied and said I was thinking about it. The truth was I'd opened a dating app on a Tuesday night, looked at it for nine minutes, and closed it again. The face in the mirror that morning had been the face of a man not ready, and I'd known it without having to argue with myself.

Three months later, the same app, the same Tuesday night, and the readiness had moved. Not by much. Enough.

This module is about that gap. The difference between when other people think you're ready and when you actually are. And then, only then, what to do about it.

Ready on your timing, not hers

The single most useful sentence I read in the first year was this: date when you'd date even if no one was watching. If you're dating to prove a point, to her, to yourself, to the mate who keeps asking, you'll pick wrong and you'll waste someone else's time doing it.

The honest readiness checks, in order:

• You can think about her without flinching. Not without sadness. Without flinching.
• You can spend a Saturday alone and not call it lonely. You don't have to enjoy it. You just have to be okay in it.
• You'd rather meet someone new than reconcile with her, today, on the actual current terms. If that question gives you a long pause, you're not ready.
• The kids are settled enough that you have an evening for yourself. Not "I'll figure it out". Settled.
• Your money has a shape. You can buy dinner and a babysitter without flinching at a $160 night.

Three out of five and you're close. Five out of five and you're there.

The apps, plainly

The apps at 35-50 are different to the apps at 22.

• Hinge. The best ratio for adults in your bracket. Profile-driven, prompt-driven, less "swipe culture", more conversation. Most matches answer questions. Most dates that come out of it are dinner-shaped, not "drinks at 10pm" shaped.
• Bumble. Solid. Slightly more polished, slightly more career-context. Women message first which sorts a class of problem before it starts. Worth running alongside Hinge.
• Tinder. Younger and more transactional than the marketing suggests. If you're 42 and looking for a co-parent of any kind, the ratio of useful conversations to time spent isn't great.
• eHarmony, RSVP. Older market, sometimes a better fit if you want to skip the swipe rhythm entirely.
• Set-ups from friends. Underrated. The hit rate is small but the hit quality is high.

Don't run more than two apps at once. The cognitive load eats your evenings and bleeds into the days you're meant to be present for the kids.

The kids question on the profile

Be honest about it. Mention you have kids in the profile, not in the third message. Anyone who's not interested in dating a man with kids will filter themselves out in three seconds and save both of you a fortnight.

A clean line: "Two kids, 50/50, primary-school-age." That's it. No backstory. No grief. No "looking for someone to complete the picture" energy.

Don't post the kids' photos. Don't name them. Don't list their schools. The internet is the internet.

The first six dates and what to actually look for

The first six dates from any app are mostly diagnostic. You're calibrating, not choosing. A few honest things to watch for:

• How does she talk about her exes? Once is fine. Three times in one date is a flag. Same flag applies to you.
• Does she ask about the kids without making them the problem? "Tell me about your kids" is great. "Will the kids be a problem?" is the answer.
• What do you feel like the morning after? Lighter? Drained? Curious? Bored? The morning-after feeling is more honest than the in-the-moment one.
• Pace. A woman in her forties who's done her own work won't push for week-three exclusivity, and she won't disappear for ten days either.
• Logistics. Can she do a Tuesday night? Can you? If both of you are too busy to schedule a second date inside a fortnight, the answer is usually that one of you isn't ready.

Don't try to know in date one. You can't, and trying to is what makes date-one men tedious to date.

The boundary about staying-overs and the kids

Build this rule before you need it.

The default for the first 6-12 months of any new relationship: she does not stay over when the kids are with you. They are not introduced. They are not told her name. The kids' weeks with you are theirs, undiluted, until you are sure enough about her that her presence in their lives won't be a transient one.

The introduction itself, when it comes, is low-key. A Saturday lunch. A walk. Not a sleepover. Not a holiday. The kids meet a woman, they say hello, they go back to their normal day. Pace the integration over months, not weeks.

This is also not a cage on you. She doesn't sleep over on Tuesdays when the kids are home; she does on Wednesdays when they're at their mum's. The rotation is built for this.

The thing nobody admits about second-time dating

It is awkward. The first kiss in the front seat of a car at 43 is awkward. The first time someone sees the slightly older body in the bedroom light is awkward. Awkward is the price of admission, not a sign you're doing it wrong.

The good news: the women you are now dating have also done a hard thing. Most of them are also slightly tired, slightly cautious, slightly hopeful, slightly braver than they were at thirty.

You are not auditioning for a wife. You are not running a scoring system. You are having dinner with another adult and seeing whether a second dinner is something you'd both look forward to.

Date when you'd date if no one was watching. Take the kids out of it for the first six dates. Buy your own coffee in the morning.

The right one will not feel like the start of the next chapter. She will feel like the second person at a table you were already eating at.

Further watching

• 5 Signs You're Healing and Ready to Date Again After Heartbreak (Psychologist)
• Dating After Divorce Opened My Eyes (Hard Truths)