I just discovered my boyfriend used to date my MOM

Dear Jane,

A few months ago I started dating a charming man who is 26 years older than me. A few of my friends and relatives thought the age difference was weird, but honestly it never bothered me. He’s still handsome, he has a great sense of humor and we get along so well.

The relationship is going so well that I planned to introduce him to my parents this weekend and while we were chatting about it he asked a little more about them.

I told him all about my mother, who had quite an eventful life, and he got a look of horror on his face. I kept asking him what was going on and he finally confessed that he and my mom dated for a few months shortly before she met my dad.

I know it’s been years, but I’m really annoyed by the idea. He insisted it was nothing serious and they haven’t seen each other in years, but I’m so shocked and put off by it I don’t know if our relationship can survive.

I haven’t been able to tell my mom because I was just so embarrassed, but she keeps asking what’s going on because I canceled our plans after finding this out.

I like this man so much and really feel like we could have had a future together… I’m just not sure I can ever get over this shocking news.

How can I go ahead and erase this information from my mind?

By,

Devastated daughter

Dear Devastated Daughter,

Your charming husband sounds delightful… but 26 years is a very big age difference.

I think maybe you’re feeling annoyed that he dated your mom might be the universe stepping in to tell you it’s time to move on.

26 years between you doesn’t mean the relationship is insurmountable, but I’ve witnessed many relationships with a similar age gap that started out beautifully and then came to an abrupt end as both got older.

You do not state your age in the letter, but the difference between a 26-year-old and a 52-year-old, while large, is nowhere near as large as a 36-year-old and a 62-year-old, and by the time you have passed their 40s – a time that many women find to be their prime – your partner will be in their 70s and probably want a much quieter life just as you’re picking up steam.

There’s a huge power differential in romances between May and December, no matter how much you may think that’s irrelevant right now. According to a 2017 study, couples with a significant age difference have less marital satisfaction after six to 10 years than couples with same-aged spouses.

That said, there are always examples of relationships that work. But with the added complication of a previous relationship with your mother, you being grossed out, and your inability to tell your parents, my advice would be to end it now before you get further entrenched.

Dear Jane,

My best friend recently confessed to me that she has been cheating on her boyfriend for seven years with a man she works with — and I’m debating whether or not I should tell him.

Yes, she used to be my girlfriend, but in all the years they’ve been dating, our friendship group has grown so close to him too.

She insists she doesn’t want to end her relationship…but also admits she has no plans to break it off with this other man any time soon. In fact, she wants the best of both worlds.

I told her she’s selfish and she should tell her boyfriend but she got incredibly defensive and told me I don’t know the finer details about her relationship and it’s none of my business.

How can I look her boyfriend in the eye again and not let him know he’s being made fun of?

By,

Stuck in the dark middle

Dear Stuck in the Dark Middle,

Oof. You try to do the right thing and you also tell your best friend to do the right thing, which seems to have gotten you little more than a best friend who I don’t think may be a best friend much longer.

If only she hadn’t introduced you.

By telling you her secret, she has now made you an accomplice to her betrayal, and that’s a terrible situation to be in, especially if you’re close to the boyfriend.

And perhaps the hardest part is that there is no way you can win in this particular situation. If you tell your friend, you will lose your best friend. If you don’t tell the friend, the weight of her betrayal will get in the way, and I imagine you’ll eventually lose her anyway.

There is no winning here, nor a clear straight path.

What feels good to me is protecting yourself. You will not lie on her behalf to her boyfriend, or even to anyone else.

This means telling her you can’t be an accomplice; that you wish she hadn’t told you, but now that she has, you can’t continue to support her as a friend unless she ends the affair or ends her relationship.

You can be there for her if and when she decides to do the right thing. But, as Maya Angelou once famously said, “When people show you who they are, believe them the first time.”