Should I date more than one man at a time?

A question that often comes up in our Dating Evolved group calls, especially when we’re talking about online dating, is

“Should I date more than one man at a time?”

It’s a fair question, and different clients have had different takes on the matter.

Angela told me, “I might be a bit old fashioned but I’m not comfortable talking to more than one person at a time, it doesn’t seem right to me. And anyway, I’d lose track of who’s who!”

Kate had an answer for that when she was dating: “I kept a little black book so that I could keep track of who said what. It suited me to talk to several guys at once so I could progress things faster.”

And here’s Caroline’s take on it:
“If you’re just getting to know people it should be fine, but I found it difficult. I felt an element of dishonesty, she said. “But if you only talk to or meet with one person at a time it’ll take bloody ages. I think it’s a balance you have to come to personally.”

It’s definitely a tricky one. On the one hand we have the way of doing things we were used to in the old days: meet one guy, start seeing him and then see how things develop. On the other, there's the newer (and some would argue, smarter) approach of multi-dating: exploring your options before investing too deeply in any. Neither is inherently right or wrong. But each has its pros and cons.

Let’s explore those…

The Case for Dating Several Men at Once

Dating multiple men doesn’t make you disloyal—it makes you deliberate. If you're in an exploratory phase, unsure of what you want or who aligns with your values, it can be good to compare options. In fact, it may be the best way to know what truly suits you.

You’re also avoiding the common trap of wildly overinvesting in the first guy that you find appealing. And the multi-dating approach is likely to be especially good for those who have anxious attachment and tend to go too deep too quickly. It’s much easier to shrug off a guy who turns out to be unsuitable when there are several other options on the table.

The drawback? It’s a lot of work: emotional labour, calendar coordination, remembering who said what. You also might feel some guilt if one connection begins to feel more serious than the rest. But as long as you’re being honest with yourself and others, you’re not leading anyone on, and it could be the quickest way of finding your guy.

The Case for Dating One Man at a Time

Focussing on one person has a lot of merit. Dating one man at a time allows you to give each connection a fair shot, and let depth develop without the noise of comparison. This approach tends to suit women who find the juggling act of multi-dating emotionally exhausting.

You also get clearer feedback from the dynamic—without interference. If things are stalling, it’s not because you’re stretched thin. It’s because he’s likely just not right for you.

But, if you’re messaging or seeing just one man at a time – as Caroline above said – it might take “bloody ages” to find your man. And while you’re focussing your attention on one person, other, more suitable men, may be entering and exiting your orbit without you noticing. The one-at-a-time method has its opportunity cost.

And bear in mind, even if you prefer the singular approach, you can't necessarily assume the guy you're with is on the same page - so have the conversation to make sure that exclusivity is mutual.

So—Which Approach Wins?

Well… it depends.

It depends on your time availability, your emotional bandwidth, and whether you’re dating to decide, or you’re dating to have some fun and see what’s out there.

Multi-dating could be best when you’re in the exploratory phase. Single-target focus is ideal when you’ve got a good candidate and you want to really get to know them. And of course you’re allowed to shift between modes. Choose the strategy that works best for you and makes you feel comfortable.

Because ultimately, dating is about finding the right guy for you — not winning a gold star for efficiency or moral purity.

So good luck, and whatever you do, try to have fun while dating!

MAIRI MACLEOD PHD

*names have been changed