Rostering, aka dating multiple people
How I help clients think about playing the field
“Should I keep dating around or focus on this one person I’m excited about?”
Most clients ask me some version of this question.
My answer: Rostering.
What is rostering?
Rostering is the modern dating practice of seeing multiple people at once.
Example: a third date with one person + a few first dates lined up.
It’s also controversial.
Some say it makes dating feel transactional or disrespectful.
Others find it keeps their spirits up, especially when one connection fizzles. For clients who get attached quickly, rostering helps them stay grounded and not spiral into fantasy.
When to roster
In general, I recommend rostering.
Dating multiple people helps you get more data, faster.
You’ll get clearer on your preferences (across the 4 Pillars of Compatibility), your patterns, and, most importantly, how you feel with different people.
(If you tend to get anxious or overinvest early, rostering also gives you emotional pacing.)
Some folks worry it turns dating into an optimization game.
But when clients focus less on checkboxes and more on how they feel with each person (what I call their North Star Feelings), the insights are often surprising.
It also helps avoid this common regret:
You go on 3 great dates, feel excited, and pause dating others…only to realize on date 6 that it’s not a fit. Now you have to restart from scratch.
This happened to multiple clients. One founder swore they’d met someone promising after a few dates. They paused new matches to focus... and came back a few weeks later saying, “I wish you had pushed me to roster.”
When *not* to roster
If you’ve committed to exclusivity, keep your word.
If dating is lower priority and your timeline is long, one person at a time might feel right.
If you lean avoidant, rostering can become a commitment-avoidance crutch. Seeing one person at a time may actually help you go deeper and build emotional safety.
Whatever your reason, be honest with yourself: not rostering = slower momentum. When one connection ends, you’ll have to rebuild your dating pipeline from scratch.
How to roster respectfully
Cap it at 3. Three people is the sweet spot: enough variety, not overwhelming. Beyond that, it becomes hard to be present or keep track. (Three dates a week is plenty.)
Keep sourcing until you’re at 3. Once someone drops off, you can resume swiping or outreach.
Be honest if asked. You don’t need to volunteer that you’re dating others, but if asked, tell the truth.
Be low-key with friends. Share how you’re feeling, not a full scouting report of your roster. This protects your own clarity.
Ask yourself why you want to roster
If you're a few dates in and unsure whether to keep looking, reflect:
Are you early in your dating journey and want more reps? → Try rostering.
Are you avoidant and scared to commit? → Get curious about what you’re afraid of.
Are you chasing the high of new matches? → Ask: How many is enough?
Are you unsure about your current person? → Rostering can clarify.
Are you doing it out of FOMO or pressure? → Maybe you’re already more invested than you think.
Whatever your choice, let it be intentional.
Share with me what happens! I’d love to hear what you learn about yourself.
Love,
Joyce ❤️🔥
P.S. My next Hot Feelings event is happening August 13 in SF. Over 175 execs from OpenAI & Stripe and founders backed by a16z & YC have attended and found dates and friends. Apply or share with a friend!