Article: How to Date Multiple People the Smart Way

Leave a comment
Advice / Essays / essays and shorts / published / Thoughts / Uncategorized / Writing

I’m back again with the guys over at Talk Thirty To Me giving you a female’s perspective on how to date multiple people. Give it a read and then get out there (and have fun!) 💃🏻

Along with all of the positive feedback on my last article Dating in Your 30s: Why You Should Date “More Than One” to Find “The One”, I also got the repeat question:

So how do you find the time to date multiple people at at a time?


Actually, it went more like this:

That’s what I have to do to get a boyfriend/girlfriend?  I don’t have time for that.  Forget it, I’m just going to be single.


I’m not letting you off that easy.  Firstly, there is nothing wrong with being single, but if you’ve decided you do want a partner – a GOOD partner (one that is honest, respectful, consistent and compatible) – then you’ll need to put forth some effort.  Nothing amazing ever happened by sitting on your ass.  That being said, it doesn’t have to take over your life and there is a smart, effective way to go about it.  For starters:

Get out there.

I don’t mean in the Trader Joe’s near the fake meat – that’s a fucking myth.  Your first criteria for dating is availability, so be where the single people are.  Some good places are: online,, singles events, speed dating.  Get over your romantic attachment to a fated chance encounter. I’m telling you how to date effectively, and I’m also telling you it is waste of time to look for love in inconspicuous places.  You wouldn’t go to a Chinese restaurant for Mexican food, would you?

Say “yes.”

No, not to everyone. To those you find attractive and interesting.  But make sure it’s to more than one person.  Your intuition is not broken.  It may be out of practice, but the more people you go out with, the better you’ll get at knowing who is a good match.

Talk to 3-8 people at a time.

One at a time causes “all the eggs in one basket” syndrome.  Two is too much like a duel.   Three is good, and beyond that, feel out your own capacity.  From my experience, anything more eight at a time is confusing because conversations start to run together.  Likely you’ll stay in Textlandia with some of these people and realistically go on dates with 3-5 of them.  And for the love of God, don’t text ALL of them ALL day.  Text when it makes sense and I guarantee this will allow for a natural flow of excitement in getting to know each other.

Schedule 2-3 short in-person dates per week with different people.

By short, I mean a couple of hours – have a drink, catch a show, or get dinner.  If it’s going well and it goes longer, cool.  These can be after work, on a weekend, whatever.  By having multiple dates lined up, you’re forced to just “fit them into your schedule,” which is all these people are at this time.   They are not your boyfriend or girlfriend yet, so don’t give them a bigger place in your life or mind.  A date is nothing more than an appointment in your calendar – but a fun one – which brings me to the most important thing…

Have fun.

The first few dates are simply unwinding after your day/week with a new friend.  So fucking relax already.  And if you’re not having fun, end it politely and go home.  You have another one lined up anyway.

Be honest.

This is as important as having fun.  Be up front about dating other people.  No need to make it weird or brag, but if it comes up or you feel the other person is overly committed, don’t lie.  Trust me.  This world is small and life is too short to stress about someone you don’t even like yet seeing you out with someone else.

Say no.

Just as I said say “yes” to who you want, say “no” to who you don’t.  If you’re not feeling someone and he or she hits you up for another date, say you’re not interested romantically and wish them best of luck.  Stop ghosting and be a goddamn adult.  Realize the same may be said to you, or you may be ghosted on.  Know it has nothing to do with you as a person and look forward to the next date.

Stop when it’s not fun.

If you’re dreading your next date or cringing at every text, it could be a sign you need to take a break.  Maybe it’s time for more “you” time – which is great.  When I found myself getting annoyed at a mere “hey, how’s it going?” it was clear I was the unavailable one. I stopped for a while – a long while – and tried again later.

Dating multiple people is lesson in abundance.  You’ll see that many people match with you and vice versa.  In the end (if that’s what you want), you choose one.  But that doesn’t mean there is ONLY ONE.  It just means you chose each other – nothing more, nothing less.  Meeting people with a scarcity mentality (ie. I need this one to be “the one”) yields scarce, and thus stressful, results.  Love is everywhere and will be there whenever you’re ready.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s