Help me settle a debate among friends: If you're someone who is more interested in a longish-term commitment than casual, no-strings-attached situations, when is it OK to date more than one person at a time?

For instance, after almost a year of blissful singledom, I met loverboy No. 1, and a week or two later, No. 2 sashayed into my life. (Both have the same first name, so here we default to the numbers system.) I like both for different reasons. If I stop seeing Bae No. 1, I know Bae No. 2 will be very interested in going "all in" with me basically right away, whereas if I choose No. 1, things would be more delicate in terms of each of us committing to the other.

Neither knows of the other's existence in my love life. How long do I have until this blows up in my face? Am I being a dick by managing these relationships the way I am? I think about the golden rule, and I know how I'd feel if I were one of these guys.

The real difference between dating and relationships is communication and our level of commitment to one another. My opinion is that when you’re dating someone, that means you’re spending time together in a mostly sexual way while still including genuine moments of bonding and discovery. (To be clear, that I don’t believe that all dates should end with sex, but two people in the casual stages of dating are usually feeling each other out for what kind of permanence they can get from each other.)

A relationship happens when two people who are dating decide to date only each other, and that’s when conversations about stuff like couples’ STD testing or future life plans come into play. People who are dating don’t share their lives with their partners on the level that committed people do, and often that includes information on whom else they might be dating.

It’s always OK to date more than one person at one time, as long as you’re just dating those people. You know, meeting up for a movie night that turns into sex and then a trip to the bar right at last call. What kind of dates are you going on with these guys? If you are bringing these people around your co-workers or family—sharing friends with whom they bond outside of your casual relationship—then that is way more intimate than dating and could blow up in your face very badly.

If you’re monogamous but still want to date more than one person, the most important thing is to keep those people completely separate from one another. They should not be from the same social scene or have an ex in common—anything like that. They should not know each other at all, really. Jealousy and territorialism are real.

That said, I hope you’ve had some sort of conversation with these guys letting them know what you’re about right now. I believe that you should always assume that whoever you’re dating is also dating someone else, but most of us don’t, and feelings often get hurt that way. You don’t have to say, “I’m sleeping with other people,” but at some point you should have made it clear to both of them that no one is committed to anyone here. Full transparency and informed consent are your best tools in this situation, friend.

I can see that you don’t want to be responsible for any broken hearts, but I can also see that you date monogamously for the most part, and you’re gonna have to let someone down eventually. Bae No. 1 sounds like he’s good in bed but commitment-phobic, but Bae No. 2 seems like someone you actually want to date. You also sound old enough to know that two people can’t build anything real around a strictly sexual bond, so stop letting Bae No. 1 dickmatize you with his prowess, and ask yourself what you really want. The choice is yours.

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