Ask Wendy

How Do I Handle Insecurities Over My Boyfriend’s Friendships with Other Women?

Friday, August 30, 2019
Hey Wendy,

I’ve been at odds about how to handle my insecurities regarding my boyfriend’s current friendship with an old (female) friend whom he had feelings for in high school.

We’re nearing the end of university and have talked about moving in together. Things are serious between us. For that reason, I want to handle the thing that causes the most anxiety for us.

He told me six months into our relationship that back when he asked me to be his girlfriend, he discussed making it official with me, with a friend he had feelings for back in high school.

They used to hang out a lot, alone, when they were both in their hometown. However, now that he is dating me, they communicate far less often than before, and don’t see each other much.

I trust that nothing physical has happened between them, but something in my gut is telling me that there are some unresolved feelings between them. Some of her actions actually are red flags to me.

For example, she’ll messaged him things I find inappropriate. She has sent him pictures of her in revealing outfits, asking him for his opinion. She asked him for help with workouts, since she wasn’t “seeing results”. He sent her videos of a certified personal trainer on YouTube demonstrating the correct form for the exercises she was doing. To that, she asked him to meet her at the gym when she’s back home at assist her. He said that he’d love to, but that she’s probably already doing fine.

Perhaps a little far-fetched, but to me, her messages made me think that she was giving him permission to touch her. This made me feel more anxious- not about trusting my boyfriend, but about trusting her.

I don’t know if I’m overreacting, or if I’m my unsettling feelings surrounding their friendship is valid. All I know is that I feel uncomfortable.

When I have told him why certain things have made me feel this way, he has told me that he would never hurt me and that because he’s known her for years, he knows her intentions would never be to wreak havoc on our relationship. He tells me he wishes that I could meet her so that I could feel more comfortable... However, I don’t feel as though he thinks that my reasoning for being uncomfortable is valid.

I’m unsure of what to do; I’m even unsure of whether or not my feelings are valid... Please help!

K.R. — Online

Hey K.R.

I understand your dilemma. It’s hard to trust, especially when another woman seems to be flirting and inviting your boyfriend to stray. It’s unnerving. But let’s set her and her advances aside for a moment.

Do you know your boyfriend to be a man of his word? Can you trust him to honor your commitment when he’s not in front of you? Think carefully, because this is the only part of this scenario you have control over.

If the answer is “no,” then you can stop reading the rest of this column and instead plan your next steps—steps that should involve either figuring out what you need in order to trust his word, or letting him go.

If the answer is “yes, I trust him because he’s honored his word in all the time I’ve known him and he has a track record of being faithful,” then great, keep reading.

You don’t have to trust her.

She’s not trustworthy.

You don’t get to control this.


You won’t be able to change or manage the parade of people coming in and out of your lives in your future that may also offer connection, be it physical, emotional, or just plain flirty. You two are out there living in the world. He’ll have a job, meet neighbors, new friends, etc., and some of those people may be attracted to him. Just as some of those people will be attracted to you.

What happens when he goes to lunch with an attractive colleague?

What if the check-out clerk at the local grocery store flirts with him?

What happens when you have kids, and he’s the hot dad soccer coach, and the other moms at the school bring him baked goods?

Does he acknowledge these women’s attentions and move on, or does he need to completely shut himself off to half of the planet?

Gone unchecked, this source of anxiety will likely only stop for you when he is no longer an attractive, sexual person. And this is going to be a problem for both of you.

We want our guy to be hot and sexy, but only for us. Have eyes for no one else. For other women to never ever turn his head or even enter his thoughts. But this fantasy isn’t tenable, or healthy.

I’m going to give it to you straight: He’s a living, breathing, sexual person with thoughts, feelings, and impulses. He will then make choices based on his own moral code and what he thinks is the right thing to do. Whether those are good or bad choices is up to what kind of person he is.

You can trade him in for another guy, but unless you’re going for an asexual guy or one with a really, really, really low sex drive, you’ll be faced with the exact same dilemma.

You don’t have to have this healthy, sexual human thing be a problem, you know. If he’s worthy of it, you can trust him and if he ever has zingy thoughts, he can transfer and direct them at you. You can be the beneficiary of such energy.

I know our culture promotes jealousy and even says possessiveness can be a good thing, right? I mean, it only shows that you love him (sigh).

Consider that it’s not good or healthy for you—not at all. Jealousy leaves everyone in a relationship in terrible shape, and nothing positive or constructive ever comes out of possessiveness over another human being.

So, let me give you a few steps to guide you on your way to handling this problem. You ready?

  1. Understand that your feelings are yours, not his to manage. It’s common to think, “I’m upset, so because you love me you need to fix it.” But no. That’s not okay. Your feelings are yours (like your toenails are yours) and they are yours and yours alone to sort through. You can ask him for help, but you can’t put it on him to fix.
  2. Stop reading his text messages, girl! They are none of your business. If you trust him, what he says to other people is none of your concern.

If #1 & #2 are not enough to put this to bed, listen to my thirty-minute How to Overcom Jealousy audio. I’ve linked it for you here.

It will give you a framework to handle jealousy for your whole life.

So that’s your part. Of course, he has a part in this partnership, too: Whatever agreements he has with you, he needs to keep them. He needs to respect that sharing certain things with you are triggering for you, and he should knock that off. You two can put your heads together and agree on what you can and cannot be expected to be burdened with in this case.

And finally, just because someone has unresolved feelings doesn’t mean those feelings will ever be acted upon. I’m not sure I know a human alive who doesn’t have “unresolved feelings” for someone. Being human is complicated, but it doesn’t mean he loves you any less.

Good luck!

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