College Advice: How Long Can I Keep Dating Several People?

Dear Veronica,

I hope you don’t find this question boring, but I can’t reach an agreement with my coworkers, and since I’m working in Chicago for the summer (and I’m from Canada), I have nobody to talk to about this.  So I think we can all agree that it’s okay to go out on first dates with several people within, say, a week, right?  But the question is: how many times can you go out with someone before you have an ethical obligation not to go out with anyone else, or at least to tell them that you’re not being exclusive?  One of my coworkers says you don’t have to tell unless you’re asked; another says even one date is too many if you’re interested in other people.  I don’t really agree with either of them, but I’m not sure where to draw the line.  Also, I’m newly single after a long relationship.  So this relatively boring question actually has some bearing on my decision-making these days.  Thanks Veronica.

- summer student

Dear Summer,

It’s funny you should raise this question — I listened in on a similar conversation among my own coworkers recently.  I think it’s something about the weather.  Like your coworkers, they had radically different opinions; but the rule-of-thumb that we eventually agreed on was that once you have sex with someone, you definitely have to come clean about everything else you’re doing; health concerns provide a simple deadline.

That said, I think it can be a lot more complicated.  Firstly, not everyone has sex within the first few dates (or at all, or before marriage, or penetratively, et cetera), and I think we’d also all agree that a year-long sexless relationship is still grounds for expecting honesty, so the rule can’t be universally applied.  And what counts as a date these days, anyway?  Sex is standing in for something here, the same way it would be an approximation if I told you that you have to disclose after four dates.  Where is that line?

I think it’s a question of the balance of insinuated promises and accrued expectations.  That is to say: I think your ethical obligation has to do with the emotional expectations that you’ve implicitly allowed the other person to hold you to.

To use an example, I think that if you tell someone that they’re the most incredible (or beautiful, or powerful) person you’ve ever met, you’re giving them reasonable grounds to conclude that you don’t want to be with anyone else.  Similarly, if you’ve told someone that you don’t believe in monogamy, then you’ve purposefully avoided creating expectations.  Sex is a good proxy because sex is when we make ourselves vulnerable to each other; and when you encourage someone to become vulnerable to you, you also assure them of your trustworthiness somehow, making their self-exposure “safe.”  It sounds more complicated than it is.  The key is to be sincere and not create expectations that you can’t be held to — don’t commit to someone if you don’t completely want to.  (In your case, don’t force it if you’re not over your ex; it’s not good for anyone involved.)

Most importantly, observe the expectations and the emotional involvement of the other person.  Even if you haven’t given someone grounds for expectations, they may still be developing them.  I know more than a few people who’ve considered themselves ethically in the clear because they explicitly told someone that they’re not looking for a relationship;  but if you’re sleeping with someone who’s in love with you, you’re still hurting that person even if you haven’t given them false expectations, and they may be too far gone to help themselves — so it becomes your responsibility.

In short: you’re accountable for the expectations you implicitly allow your date or your sex partner to develop.  And if you figure out that your partner isn’t safeguarding his or her emotions responsibly, you’re responsible for their feelings, too, sort of the way a medical proxy is responsible for someone who’s not capable of making decisions.  I believe that when you go out with someone even once, you’re consenting to becoming their emotional health proxy as far as your own relationship is concerned.  The first implied promise of all relationships — your prime directive — is to protect the well-being of the other person as much as you can.  I think that rule transcends gender, orientation, identification, and age.

I’ve tried to articulate my view logically, but I hope this makes intuitive sense.  Look, you know when the things you’re telling someone ring false with your real level of commitment; just don’t do anything that doesn’t feel sincere.  (I know how hard this can be on the awkward first few dates, but you have to try.)  And have fun!  Chicago’s a great city (I imagine)!

-VVM

Send me your questions anonymously by writing to VeronicaMittnacht@thefastertimes.com