Dr. Wes and Kyra: My boyfriend insists that talking to his girl best friend is perfectly okay and I should not feel jealous. However, he and she used to hook up and even considered dating. He says I shouldn’t worry as “they can’t date because it just wouldn’t work out.” How am I supposed to accept this?

Wes: You’re not and I’d argue that not accepting it has nothing to do with jealousy. It has to do with him not respecting what it means to be in an exclusive relationship. Few things mystify me more these days than the idea that people can break up and “just be friends” or that people, who would otherwise be sexually attracted to each other, can just hang out and not expect dating partners to see it as problematic.

Younger readers might request that I come into the twenty-first century and advance my thinking on this: that teens and young adults today are sophisticated enough to manage a romance and a friendship without incident. I might actually do that, if I ever saw it work out well.

On the rare occasions when it doesn’t create a dating nightmare and ultimate breakup, the non-dating friendship must fulfill two criteria:

1. The friends must never have dated, nor considered dating, nor hooked-up, and there’s very little sexual attraction between them. In fact, I will often ask the person who is proposing this kind of friendship: “How many of these do you have in which you find your friend physically unattractive?” The answer is always “none.” This is because people like to be friends with attractive partners whether they take the relationship to the next level or not. That leaves these relationships always hanging about one click away from romance.
2. The friendship should include both dating partners, not a side relationship with that exists in isolation from one or the other. If you’re all part of the same friend group and you’re as close to your partner’s friend as he or she is, then sometimes (underline s-o-m-e-t-i-m-e-s) this can work. Other times, it creates the love-triangle storm of the century.

From what you’ve described, neither criterion apply and your guy is wrong to expect you to take this relationship in stride, as Kyra points out next.

Kyra: While I do not advocate jealous helicopter crazy girlfriend-ing, this situation stretches beyond just a boy and a girl dating and the boy also having a close female friend. Even if they never put a label on it, their hooking-up counts as a past relationship. Your boyfriend probably wouldn’t appreciate you watching a romantic comedy in an ex-friend-with-benefits’ basement under the pretense of being “just friends.” Your guy shouldn’t expect you to be okay with the reverse.

You say he claims they couldn’t date because it “just doesn’t work out.” Great, except at least some part of their relationship worked if they’re still talking regularly. I don’t know how long you’ve been going out with him, but it sounds like he still might not be over her. I would take their recurrent interaction as a red flag.

Your boyfriend seems to have a different perspective since he doesn’t think your jealousy is merited. Wait for a neutral time and place to broach the subject. Nothing productive will come from approaching him right after he spends time with her or if you catch them texting. Calmly explain that his extensive conversations with his once-physically-intimate-partner are upsetting and hurtful. Then let him decide which relationship is more important to him. If he doesn’t change his ways, break it off. Ultimatums usually aren’t cool, but in instances like these, they may well be necessary.

The combination of jealous feelings on your end and resentment on his can only result in more negativity as the relationship limps along like a zombie, waiting for whatever it is that zombies wait for. Even though my personal search has been mostly fruitless, I cling to the belief that there are plenty of great guys with whom to snuggle, many of whom CAN let their exes go.

Wes Crenshaw, Ph.D., ABPP, is author of “I Always Want to Be Where I’m Not: Successful Living with ADD & ADHD.” Learn about his writing and practice at dr-wes.com. Kyra Haas is a Free State High School senior who blogs at justfreakinghaasome.wordpress.com. Send your confidential 200-word question to ask@dr-wes.com. Double Take opinions and advice are not a substitute for psychological services.