How To Talk To Your Friend About Their Questionable Dating Behaviors

When is it OK to tell them their dating habits are toxic as all get-out? Therapists weigh in.

Boundaries matter in friendship. You wouldn’t, for instance, tell your friend that the undereye filler they just spent $700 on was a total waste of money. Or that they’re reaching Donald Trump levels of over-tweeting and may want to give Twitter a break.

But what boundaries should you stick to when it comes to discussing their relationships and dating habits? When, if ever, are you free to express your distaste for the people they’re seeing? When is it better to just cover your eyes and let the impending train wreck happen, as much as it hurts to foresee it?

More often than not, err on the side of zipping it, said Alena Gerst, a psychotherapist in New York City. That’s especially true if your complaint is about the person they’re dating.

“If you simply don’t like the new person, it’s best to keep it to yourself,” she said. “Even if you’re the closest of friends and deeply value each other’s opinions, it will likely put a wedge in your friendship, and make your friend feel less willing to come to you if they do have real problems if the new relationship gets serious.”

Yep, that means you’ll have to wait until the breakup to tell your friend that her new boyfriend Chris is a total clown.

Criticize your friend's dating habits at your own risk, experts say.
Tim Robberts via Getty Images
Criticize your friend's dating habits at your own risk, experts say.

Yes, there is an exception for a friend who’s in danger.

Obviously, there are exceptions to this rule. If you suspect there’s violence or emotional abuse in your friend’s burgeoning relationship, voice your concerns right away and make yourself available to help in whatever way they need.

How do you know if your friend is in an emotionally abusive relationship? It often starts with someone blocking the people once closest to them from their lives in favor of their new S.O. It’s natural for new couples to get swept up in their relationship and devote all their time and energy to each other, but if that increasingly comes at the expense of family and friends, the resulting isolation could be a problem, Gerst said.

“That’s not healthy on its own, but it’s also a common tactic that abusers use in order to gain more control over their victims,” she said. “Check in and let your friend know you miss them. You can also try to get more information about whether or not they are being treated well.”

So you have a free pass to broach toxic relationship patterns. But if you bring up less consequential issues, you run the risk of pushing your friend away over something that’s more irritating than dangerous. Take it from Westfield, New Jersey, therapist Melissa Cohen. In her 20s, Cohen had a close friend who was in a relationship with a man who left a lot to be desired. Cohen said he was often dismissive of her friend’s feelings and behaved embarrassingly in front of friends and family.

“Even if your friend directly asks you for advice, the better route is to ask non-judgmental questions to help your friend come to their own version of clarity.”

- Melissa Cohen, a therapist in New Jersey

“Week after week she would complain to me about this,” Cohen told HuffPost. “One day she showed me a six-page breakup letter that she had written to him. She seemed clear in that moment that it was time to end the relationship but she was still scared of being alone.”

Cohen made the mistake of weighing in with advice, telling her friend that if she had six pages worth of reasons to break up but only one reason to stay ― her fear of being alone ― she should end it.

“I thought I was being supportive. Unfortunately, she wasn’t really ready to leave the relationship,” Cohen recalled. “She suddenly stopped talking to me because she felt I did not support her decision. Eventually, the man broke up with her but we never reconnected.”

Another exception comes when your friend asks for advice.

If your friend actively seeks to hear your thoughts on their personal life, you can take a different approach: Offer advice, but do it gingerly.

“Even if your friend directly asks you for advice, the better route is to ask non-judgmental questions to help your friend come to their own version of clarity,” Cohen said. “After all, you can’t possibly know how you would be in their situation because you aren’t the one feeling what they feel or thinking their thoughts.”

If you’re dead set on giving advice, test the waters first by asking if they’re interested in hearing your thoughts, said Marie Land, a psychologist in Washington, D.C. Again, do it tactfully.

“You can say something like, ‘When you’ve been talking about X lately, I’ve been wondering if I should just support you or if you want my advice,’” Land said. “That doesn’t mean they’ll be OK with what you say, but you have a little more leeway in giving your opinion than from out of nowhere.”

Before giving your two cents, offer a disclaimer, Gerst said.

“Let them know you are not in their position so can’t fully understand what they are going through,” she said. “Invite them to call you out if you’re missing the point or your perception is all wrong.”

Come to it from a judgment-free place, Cohen said. If your friend is in a “situationship” or keeps mistaking casual sexual encounters for actual connections, let them come to that conclusion themselves by talking it out with you.

Finally, don’t try to channel your inner armchair therapist here. Approach the conversation with curiosity rather than as the expert, Gerst said. (You probably wouldn’t want your friend trying to micromanage your personal life, right? It can feel patronizing.)

“Resist the urge to assume you know everything that is going on. Ask questions and listen,” she said. “If your friend brings up something that is new, ask them for more information about it. Listen more, advise less.”

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