I’ve met the person of my desires… if he discovers my soiled little secret, he’ll be disgusted: DEAR JANE

Dear Jane,

I have been dating the man of my dreams, but there’s one thing in the back of my mind that I just can’t shake.

I have cheated on pretty much every man I have ever dated – and my current partner has no idea.

Though, to be clear, I’ve never cheated on him.

I was a bit of a wild child before meeting him, but once I did, I was inspired to completely turn my life around and be a better version of myself.

He keeps me grounded and has made me genuinely enjoy a slower, calmer lifestyle, rather than my old, hard partying ways.

But now that we’re getting more serious, I’m conflicted about being completely transparent with him and revealing my past infidelity.

While he knows about my party girl phase, I’ve never confessed to cheating, and I’m worried if I did, he’d never see me the same.

Truth be told, that isn’t the kind of person that I am anymore – and I don’t want him to judge (or hate!) an old version of myself.

But in keeping it from him, I also feel like I’m lying – and I know if the roles were reversed, I’d probably want to know.

Is it wrong to never tell him, or do I need to disclose it?

Sincerely,

Former Cheater

Dear Former Cheater,

Let me start by saying that the very fact that you are wrestling with this issue tells me how far you have come. The old version of you might have asked yourself how you could get away with it, whereas this new, mature version is asking yourself what kind of partner you want to be.

You are under no obligation to confess every past mistake. You haven’t cheated on him, nor are you hiding a current betrayal.

That said, I understand the burden of what you are carrying. What I’m sensing behind your words is that you want to have an open and honest relationship with this man, and, perhaps more importantly, to relieve yourself of the guilt of your past.

But ask yourself this: would telling him do more harm than good? In this case, while it might ease your own conscience, it might also potentially destabilize your partner’s sense of security.

I would ask you to reframe the narrative from ‘I’ve cheated on everyone I’ve ever dated’ to ‘I used to sabotage relationships because I was chaotic and immature.’

Having said that, I do think it would be wise to have a conversation. If you don’t, he might hear it from someone else and, without context, assume that you’ll do the same to him.

Tell him that there is something in your past you have struggled with and that you are not proud of. Tell him that since meeting him, you have changed and grown, and this relationship has made you want to be a better person.

I understand how frightening it is to reveal our secrets. We carry so much shame around them, we worry that if someone knew, they would leave.

Being vulnerable enough to hold that shame to the light is terrifying, but freeing. If he is the right person for you, he will understand. And if he judges you and chooses to leave, then he is not the man for you.

Dear Jane,

My husband and I have been trying to get pregnant for months to no avail, and it’s been heartbreaking.

But that’s not why I’m writing in.

You see, my best friend is, in fact, pregnant and throwing a baby shower for herself.

She expects me to be there, but being surrounded by the bassinets, bibs and rattles will surely devastate me.

It has always been my dream to be a mom, and as happy as I am for my friend, I don’t know if I’ll be able to show up for her the way that she needs me to. If I try to tell her though, she might feel like she can’t talk to me about her pregnancy, which I don’t want either.

I’m torn between going and holding back my emotions or apologetically declining the invite.

The latter, however, will likely make her furious, or at least very hurt, and I know I’ll regret it years from now if I don’t attend.

Do I suck it up and go? Or, if I decide to skip, how do I kindly tell her the situation without making her feel bad?

Sincerely,

Baby Blues

Dear Baby Blues,

This is such a tough situation, and one that I remember well, from the other perspective.

When I got pregnant with my first child, my best friend was pregnant at the same time. We went through everything together, reading the same pregnancy books, comparing notes, sharing our excitement.

A few months into our pregnancies, she tragically lost her baby, and disappeared from my life.

There were no conversations about this, and I fully understood that it was immeasurably painful for her to remain witness to my ongoing healthy pregnancy. But I was devastated.

And so, I understand your pain at being around the very thing that you want more than anything else in the world. Any prospective mother would.

What’s more difficult to understand is the complete disappearance of a friend you love, so I think there is a middle ground here.

I do not think you should put yourself through the baby shower, nor do I think your friend will be furious. We often dread doing the difficult thing, assuming people will be devastated or angry, but often, once we do it, we find their reaction is not at all what we expect.

Telling your friend that you love her, but that it will be too painful for you to be present may be hurtful, but if she is truly a friend, she will understand.

You can send a lovely gift for her to open, and continue checking in with her and sharing her joy.

All friendships hit bumps in the road, and however hard we try, there are times when we will let down those we love. But, if the friendship is a real one, she will understand and your openness and clarity will pave the way for a deeper, more open relationship.