Ask Wendy

My Boyfriend Won’t Set Boundaries with a Female Friend – Help!

Friday, January 18, 2019
Hey Wendy,

I’ve been in a happy relationship for almost seven months now, and it’s pretty serious. We’re both in our late forties, have solid careers, and tidy endings to our first marriages. My guy has been divorced now for over ten years, and his ex-wife is lovely.

Here’s the problem: Several years ago, my boyfriend met a woman who turned into a friend who trains for Marathons with him. She’s about 10 years older than he is, says she’s in love with him, and has been the #1 reason for every breakup he’s had since she’s known him. He says they’re platonic, and he’s told her that nothing would ever happen between them because he’s not attracted to her.

She acts like a jealous girlfriend (calling over and over until he picks up, berating him, etc.) and he lets her do it. He’ll say, “I better pick up or she’ll just keep calling.” He doesn’t have any boundaries with her. He’ll even talk to her at really inappropriate times (like when we’re being intimate).

A marathon is coming up and they’re in training now. It’s been awkward since they are used to sharing a hotel room. He asked me if I was okay with it, and I’m not. He told her, “I can’t share a hotel room with you because Sarah has an issue with it.” He’s willing to put in boundaries when I’m to blame. And he said he would break off the friendship with her if I need him to, but I don’t want to be the cause of a friendship ending, but I don’t like what’s happening either. Help!

Sarah D., San Jose, California

Hey Sarah,

I take issue with this woman being the reason every one of your guy’s previous relationships ended. It’s not her who’s the problem—it’s your guy.

Let me help you out here. Instead of responding to you, I’m going to talk to your guy for a second. Please print this column out and hand it over to him. Okay?



Come on.


Why are you doing this to your girl?

Why are you putting her in the middle of this?

Let’s be honest. You see what’s going on. Do you really want another good relationship to end because of your inability (or lack of desire) to establish and hold boundaries with this friend of yours?

If you were 17, your actions would make sense. But you’re not 17. You have learned how to adult, and you’re now a grown-ass man. You know how to nip this in the bud. You’re aware of the “ignore” feature on your phone. You grasp the fundamentals of voicemail. You have the capacity to say, “I’m in a committed relationship, so sleeping in a hotel room with you is no longer an option for us.”

Do you realize you’re still in the courting stages of this romantic relationship with Sarah? This is not locked down yet. Sarah is looking at you to see if you’re a good bet for a long-term relationship and/or marriage. She’s still checking you out. And right now, you’re showing her exactly what she can (and can’t) count on you for—and my friend, it’s not looking good.

Here’s what you’ve taught Sarah she can count on you for so far:

  • Creating drama when there’s no need for it
  • Exercising poor judgment
  • Putting unwarranted blame and responsibility on her
  • Not making her feeling safe and respected a priority for you
  • Not having the emotional intelligence to recognize the damage you’re doing here

Is feeding off the energy generated by your friend’s possessive antics worth the cost?

You’ve basically set Sarah up to either be the doormat who puts up with this bullshit, or the bitch who ended your friendship. She can’t win here, and it’s kind of a dick move on your part.

Good news! Since this is your fault, you can fix this. We know you can do it, and we’re counting on you! Don’t “let” people do things to you. You are the boss of your show. Own who you are and what you can and can’t make happen in the world. Create agreements with your sweetheart so you get what you need and she gets what she needs to feel safe and secure in this relationship, as well. You want her to feel safe and happy and loved, right? (Pssst, you’re failing at that right now.)

Your girlfriend is much kinder and more patient than me. You want to be grateful for her generosity here. If I were dating you, the first time I ever saw such a blatant lack of accountability for your own choices, I’d have said, “Oh, okay, you let everyone around you run your life so that you don’t have to be responsible for anything. Cool. It was really nice to meet you. Have a great life!”

Look, I’m sure you’re an amazing guy. Probably pretty handsome, funny, smart, and all the rest. But this piece here? You have to work this out, or you’re going to lose her over this. It’s an absolute deal-breaker for any good woman, and I’m guessing you want a good woman in your life.

Also: Once you’ve squared things away with your marathon friend, apologize to Sarah, thank her for her patience, and take her out for a nice meal or a weekend getaway or something.

No need to thank me for this sage advice, but you’re welcome.

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