Dating as a Single Dad (Harder Than It Looks, and Not for the Reason You Think)

Dating as a single dad sounds like a problem with an obvious cause. Children. Small, loud, sticky, expensive children, who arrive with a complete operating schedule and no interest in your love life. Surely they're the obstacle.

I don't think they are. I think the children are the least complicated part of the system.

The real constraint is the calendar. Think of a single parent's week as a fully booked schedule with one or two free slots, both of which are contingent on someone else's availability. A babysitter, a grandparent, an ex-partner who has to swap a weekend. Every date is a small distributed-systems problem. Both parties have to be free at the same time, and one of them has a hard deadline: the sitter turns into a pumpkin at eleven.

That does something odd to the dating itself. There is no room for the leisurely, let's-see-where-this-goes first date. You get one evening, perhaps two a month, so each one carries an absurd weight. It's a job interview conducted over a nice dinner, by two people who are both too tired to be charming.

The second constraint is guilt. Every hour spent on a date is an hour not spent with the kids, and the maths of that never quite resolves. A good evening feels like a small betrayal; a bad one feels like a waste of the babysitting fee and the guilt. Either way, you come home and stand in the hallway listening to the silence of a house where nothing happened, and you wonder whether any of it was worth the trouble.

That's not pathos. It's just the price of caring about two things at once.

The third is the story you tell yourself. The single dad is a figure with a lot of cultural baggage. He's either a saint, which is exhausting to live up to, or a cautionary tale, which is worse. Neither version leaves much room for the ordinary person who would just like to meet someone he finds interesting. So he overthinks it. He rehearses how to mention the kids. He drafts the message and deletes it. He turns a text about Thursday into a six-hour project.

Here's the part nobody mentions, though. The constraints are also a gift. A single dad with limited time has very little patience for games, performance or ambiguity. He's already run the numbers on what an evening costs, so he tends to say what he means. People who date him often find that refreshing, which is a polite way of saying most of the other men they've met were wasting their time.

So is it harder than it looks? In logistics, absolutely. In everything else, it's the same business it always was: find someone you like, be honest about your life, and see whether it fits. The difference is that the margin for error has shrunk, and a margin that small makes everything funnier, if you're willing to look at it that way.

Which, I'd argue, is why the situation is such good comic territory. Take a competent adult, give him a job, two children and one free Friday, and ask him to be romantic on a deadline. You don't need to invent anything. Reality does the writing.

A novel about this

That's the engine of Who Needs Love, Anyway?. Danny Watts is forty-two, twice divorced, raising two kids and managing a tech support team, and he's concluded that romantic love is mostly something people are sold. His attempts at dating go wrong in ways that are both specific and wildly inventive, which is exactly what happens when a man with no spare time tries to improvise.

It's dad lit with a real heart under the jokes, and a book that suspects Danny's cynicism is covering for something. If you've ever tried to be charming between a school run and a bedtime, you'll recognise the weather.