Five things I learned from a very bad first date

I'd like to say the evening peaked early. It didn't peak at all. But bad dates are excellent content, so let's call it research.

Dating long enough gives you stories. Some are romantic. Some are hilarious. Some make you question every decision that led you to sitting opposite this particular human being on a Thursday evening.

And occasionally, you get a date so spectacularly bad that the only sensible thing to do is extract the lessons, tell your friends and make sure it wasn't completely a waste of a good outfit.

So, in the interests of public service, here are five things I've learned from some of my worst dating experiences.

1. When someone tells you who they are, listen

A man who tells you what he's “not looking for” in the first ten minutes is actually being rather generous. Believe him immediately.

I've definitely been guilty in the past of hearing something on a date and mentally translating it into something more compatible with what I wanted.

“I'm not looking for anything serious right now” becomes he just hasn't met the right person yet. “I'm terrible at texting” becomes he's probably just busy. “I don't really do relationships” becomes perhaps things will be different with me.

No, babe.

Sometimes people really do give us the information we need. The problem is that chemistry, attraction and optimism can make us remarkably creative interpreters.

You don't need to convince somebody to want the same kind of relationship you do. Listen to what they're telling you. It can save you months of confusion.

2. Basic manners are not “high standards”

I've had a man leave a date while I was in the bathroom. Yes. Actually leave.

One minute you're touching up your lipstick, the next you're apparently starring in your own low-budget episode of Where Did He Go?

Was it embarrassing? At the time, absolutely. But here's what I eventually realised: somebody else's appalling behaviour isn't evidence that there is something wrong with you.

The same applies to people who are rude to waiting staff, spend the evening staring at their phone, turn up ridiculously late without apologising, make inappropriate comments or behave as though giving you their undivided attention for an hour deserves some sort of medal.

Wanting someone to treat you with courtesy isn't demanding. It's the absolute baseline.

And if they're struggling with the baseline on date one, when most people are supposedly on their best behaviour, I'd pay attention.

3. Don't give a first date main-character preparation for a cameo appearance

You know the routine. Hair washed. Outfit options covering the bed. Makeup done. Nails checked. Perfume applied. Friends consulted about shoes. Possibly a small military operation involving fake tan.

And then... nothing. Because he hasn't confirmed the bloody date.

I've learned this one the annoying way: don't invest heavily in plans that haven't been made. If somebody hasn't confirmed the time and place, I'm not spending two hours getting ready on the assumption that they eventually will.

It isn't about playing games or pretending not to care. It's about valuing your own time. Your evening matters too.

Make other plans. Pour yourself a glass of wine. Wash your hair tomorrow. But don't sit there fully dressed at 7pm staring at WhatsApp and wondering whether “I'll let you know” somehow became a confirmed reservation.

4. There are some things you should never have to explain are inappropriate

I've experienced a few moments on dates where my brain has genuinely needed several seconds to process what I've just heard.

One man offered me £100 to have sex with him in his car. Another asked whether I'd be interested in having a threesome with him and his roommate. Romance, apparently, is alive and well.

Now, I'm not remotely prudish. Adults can want whatever they want, and consenting adults are perfectly entitled to arrange their relationships and sex lives however they please. But context matters.

There is a rather enormous difference between two people discussing something they're mutually interested in and somebody you've barely met dropping a sexual proposition on you as though they're asking whether you'd like another glass of Sauvignon.

You are allowed to find something inappropriate. You are allowed to say no without softening it. You are allowed to leave.

And you absolutely do not owe somebody an apology because they made the situation uncomfortable.

5. An outrageous accusation is an excellent reason to end the date

And finally, perhaps one of the most bizarre. A guy once couldn't find his wallet. His immediate conclusion? I'd stolen it.

Not “God, where did I put my wallet?” Not “Maybe I left it at the bar.” Not even the traditional frantic pocket-patting routine.

No. Apparently the most logical explanation was that the woman he'd invited on a date had embarked upon an elaborate criminal enterprise to acquire his wallet. Reader, I had not.

And this is perhaps the biggest lesson I've learned from bad dates: you don't have to stay and rehabilitate someone's opinion of you.

You don't need to prove you're nice enough, trustworthy enough, relaxed enough or sufficiently “cool” about behaviour that is completely unacceptable.

Sometimes the healthiest response isn't to argue your case. It's to recognise that this person has just given you some extremely useful information and act accordingly.

The real lesson?

Bad dates used to make me wonder what I'd done wrong. Now I see them very differently.

Dating isn't an audition where you're desperately hoping somebody chooses you. You're gathering information too.

How does this person communicate? Do I feel comfortable around them? Do they respect boundaries? Are they curious about me? Do their words match their behaviour?

And, quite simply, do I actually like them? Because that's the question we sometimes forget to ask when we're too busy wondering whether they like us.

Some dates become relationships. Some become friendships. Some become stories you tell over wine for the next ten years. And some become blog posts. So perhaps none of them are entirely wasted.

Pretty Little Tease verdict: keep the standards. Keep the sense of humour. And if a man accuses you of stealing his wallet on the first date, there probably shouldn't be a second.

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Enjoyed this one? There’s plenty more where that came from… ♡

Dating stories, confidence, relationships, friendships, life lessons and all the things I’d probably tell you over a second glass of wine.

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