Why I Can't Date Multiple People

If comparison is the thief of joy, then I'm an easy target for muggers.

If all the dating manuals I’ve read (and trust me, it’s a lot) have something in common, it’s that they advise us, in the early stages of relationships, to ‘date multiple people’.

In theory it makes perfect sense. By not putting all one’s eggs in one basket, you lower the stakes surrounding each developing connection, helping one to convey the persona of cool ‘ice queen’ (in the words of Bridget Jones) which inevitably increases the chances of successfully attracting a man. The impact of the blow that comes from the end of one fledgeling relationship will be diminished by the line of potential suitors taking you out to dinner on the other days of the week. Heartbreak averted.

One dating guide I found likened the process to test driving a car. ‘Would you buy the first car that you test drive? Or would you test drive multiple cars to see what features it has?’ It seems like sound logic.

But people aren’t cars. And even if they were, my answer to the first question—would you buy the first car you test drive—if it met all my requirements, would likely be ‘yes’. I will admit I’m someone who trusts my gut perhaps more than they should, yet I know from talking to friends I’m not the only one who feels like this.

Deep down I think we often know early on which of our ‘options’ we want to progress. I usually know from the first date. So from that point onwards, dating other people feels disingenuous.

Now there’s a difference between being attracted to multiple people, even hooking up with multiple people in a short space of time, and dating multiple people. I am very capable of the former. But it is only when this attraction moves into the realm of action and emotional vulnerability that for me it starts to feel uncomfortable.

On more occasions than I’d like to admit, I’ve found myself lying in bed with one person, pretending it’s someone else. This is horrible and I’m not proud of it.

All this before even considering that with a work life which takes up about 80% of my mental capacity during the week, half the time I feel hardly capable of dating one person at a time, never-mind two.

Which brings me to my current dilemma…

A couple of weekends ago, I had a lovely date with a boy I’d met at a party. This boy is also best friends with my best friend’s boyfriend, which makes the whole situation quite appealing (imagine all amazing double dates we could have!!).

As we sat down at the table with our pints, he said, “J said we should sit beside each other on the date, not opposite, apparently you have a thing about that.” I laughed. It was true. I was convinced this exact issue had stifled the potential for flirting on several dates I’d previously been on. “Gosh, what else did she say?” I asked. He started to reel off the list of icks I’d previously mentioned to J, which included mentioning the gym too much, and wearing a gilet.

It was objectively a brilliant date. He very successfully avoided all of my icks, and sat next to me, not opposite me. When the bell for last orders rang, I asked if he’d like to come back to mine for a *cup of tea*.

Never sit opposite each other on a date.

The next morning after he left, my housemates asked me how it was.

“It was so great, he’s great.”

“I feel like there’s a but coming…”

“Well yeah, I can’t help but think about how I prefer [insert Scottish boy’s name here].”

This scenario can hardly be described as dating multiple people. Things with the Scottish boy had been left open-ended, but with little prospect of materialising in the near future. It shows, however, that even going on multiple first dates in relatively short succession leads us to make direct comparisons.

I have planned to see the boy from the party again. I have justified this to myself on the basis that I shouldn’t make a judgement on the basis of comparison after one date, that I should persevere and get to know him, because my current approach to dating, based on gut instincts fuelled by what I suspect are avoidant personality traits, clearly hasn’t been the most effective so far.

But in doing this, I still feel that I have a lot to grapple with. Maybe comparison does after all serve a purpose, in that it confirms or denies our feelings, our instincts. But then, by definition, in doing this, we are also using someone. Using someone to seem chill and laid back and not-too-available, to inspire feelings of jealousy, to confirm our instincts which we probably knew already. This is why the idea of dating multiple people baffles me (and why I have never successfully managed it).

I guess whether you date multiple people or not, comparison will always rear its ugly head. It’s only human nature to want a frame of reference to base our decisions on. I guess that’s why we date in the first place, to get an idea of what we like and dislike, our icks, to know what’s out there. The comparisons we make may not always be fair or right—I suspect I will always romanticise the idea of relationships that I can’t have, or the boys I know are walking red flags, although that’s a story for another day…

Have you tried dating multiple people simultaneously? How did it go? I’d love to hear all about it in the comments.