Ask Wendy

My Family Doesn’t Approve of My Boyfriend, Help!

Friday, October 11, 2019
Hey Wendy,

For the past few months, I have been dating a guy who has a brother who is dating my cousin (4 years strong).

He is 35 and I am 23. He is getting a divorce, and he has a criminal past, but the last crime he committed was 10 years ago. If not for the fact that his brother is dating my cousin, I would be much more skeptical, but she has never had anything bad to say and I am confident if there were bad things to say she would tell me.

My family is adamantly against the relationship and says: he is too old for me, I should be more skeptical of his past, no one they know has anything good to say about him, and that because of some issues some family members had 20 years ago, I should not see him.

I am conflicted. I’m afraid of the rifts it would cause in my relationships and have had a lot of anxiety about the situation. I am also hurt that we weren’t given the chance to reveal his past and be as transparent as he has with me about it. Any good advice?

Heather R.

Hey Heather,

Thanks for bringing me this question. I think the best I can do is show you what to pay attention to and what to get curious about.

First off, I bet your boyfriend is really cute. Funny. Charming. Smells good. He melts your heart, and heats up other parts, yes? Did you know that rose-colored glasses come standard issue with every new relationship? It’s true. Don’t think I’m singling you out — we all wear them for the first few months or so. Consider, you don’t see what your family sees, and maybe they’re trying to save you.

So, your family… Do they want you to be happy, safe and loved? Or are they assholes out to make your life as boring, miserable and lonely as possible? Do they give you a lot of bad advice? Or can you count on them for sage wisdom when it comes to life matters? How credible are your family members when it comes to their opinions?

Next, consider you haven’t heard anything bad from your cousin not because there’s nothing there, but maybe because she thinks it’s a) not her business and b) your lesson to learn. Maybe she doesn’t want to hurt you. Maybe she’s just not that good at being direct and doesn’t want to cause a rift with you. Maybe she knows every human around you is trying desperately (and failing) to be heard by you. Maybe she doesn’t want to get shot, you know, as the messenger.

A twelve-year difference isn’t the worst thing I’ve ever heard when people are older. But at 23 and 35? That’s pretty far apart. You might think you are at his intellectual level, but he’s got a half a lifetime on you. If he is your equal, I’m concerned, and if he’s not, I have a different set of concerns — you should too.

He hasn’t broken any laws (that we know of) in the last ten years, yay for him. And sometimes people get into situations or make bad choices, I get it. But what I’m curious about is where his head is today? That’s equally if not more important than what he did back in the day. What caused him to break the law in the first place? Is he remorseful? Does he blame others for what happened to him? Is being a scofflaw part of his personality?  Perhaps the criminal history isn’t the thing your family objects to, but what might come in the future due to his disposition, demeanor or attitudes – interrogate the shit out of that, will you?

I’d take a hard look at why no one has anything nice to say about him. Huge. Flaming. Red. Flag.

And let’s not skip past the mysterious “thing” that happened with those family members 20 years ago. I’d definitely get underneath that one.

Due diligence is prudent in any new relationship. You want to ask and answer the following questions:

  • Does he have what I need in a partner to help make me feel safe, loved, happy, free and empowered?

Yeah, yeah, yeah, I know. It’s OUR own responsibility to feel safe, loved, happy, free and empowered. However, being responsible for this yourself means you need to do a superb job of handpicking the right individuals to hang around you.


  • Do I respect him for who he is right now (not who he’s going to be someday)?
  • Do we get each other easily?
  • Does he value what I value?
  • Does he have a high level of integrity?
  • Does he mean well?
  • Does he have good, long-standing friendships and good rapport with his exes?
  • Is he self-reflective and does he take responsibility for what has happened in his life?
  • Do we have matching emotional intelligence and communication styles?

The stress and anxiety you’re feeling is real. I’d like you to shift your thinking from “him or them” to “they want what’s best for me, I’ll take their words under advisement.” Adulting means you get to make your own decisions and stand your ground. And you shouldn’t have to choose one over the other.

I have given you a shit-ton of questions to answer here. Is it way too overwhelming? If no, then you’re welcome! If yes, consider you’re not ready for partnership, and instead, flip to friendship or date for fun. Get on birth control and have him wear a condom.

Good luck!

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