I just found out my boyfriend used to date my MOM

Dear Jane,

A few months ago I started dating a lovely man who is 26 years older than me. Some of my friends and family found the age difference strange, but to be honest, it’s never been something that bothered me. He’s still handsome, has an amazing sense of humor, and we get along great.

The relationship has been going so well that I was planning to introduce him to my parents this weekend and while we were chatting about it, he asked me a bit more about them.

I was telling him all about my mother, who has had quite the eventful life, and he got a look of horror on his face. I kept asking her what was wrong and she finally confessed to me that he and my mom actually dated for a few months shortly before she met my dad.

I know it was years ago, but the thought sickens me. He insisted that it was nothing serious and that they haven’t seen each other in years, but I’m so horrified and disgusted that I don’t know if our relationship will survive.

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

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

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

Of,

devastated daughter

Dear devastated daughter,

Your lovely man sounds lovely… but 26 years is a big age difference.

The international best-selling author offers sage advice on the hottest topics for DailyMail.com readers in her weekly column Dear Jane, Dying Aunt

I think maybe the fact that you’re grossed out by him dating your mom may be the universe is 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 great and then came to a rocky end as you both got older.

He doesn’t give his age in the letter, but the difference between a 26-year-old and a 52-year-old, while big, isn’t as big as a 36-year-old and a 62-year-old, and by the time he gets to In your forties, a time many women are discovering to be their prime, your partner will be in their seventies, probably wanting a much quieter life just as they’re picking up their pace.

There is a huge power difference in romances from May to December, as much as you think it may be irrelevant now. After six to 10 years, according to a 2017 study, couples with a significant age difference have less marital satisfaction than those with spouses of a similar age.

That being said, there are always examples of relationships that work. But with the added complication of a previous relationship with your mother, being grossed out, and not being able to tell your parents, my advice would be to break up now before you entrench yourself further.

Dear Jane,

My best friend recently confessed to me that she’s been cheating on her boyfriend for seven years with a guy she works with, and I don’t know if I should tell him or not.

Yeah, she was my friend first, but in all the years they’ve been dating, our friend group has gotten really close to him too.

He insists that he doesn’t want to end their relationship…but he’s also admitted that he doesn’t plan on breaking up with this other guy anytime soon. Basically, she wants the best of both worlds.

I told her she was being selfish and needed to tell her boyfriend, but she got incredibly defensive, telling me she didn’t know the finer details of their relationship and it was none of my business.

How can I look her boyfriend in the eye again and not let him know he’s being played for a fool?

Of,

Caught in the cloudy middle

Dear caught in the cloudy middle,

Phew. You’re trying to do the right thing and you’re also telling your best friend to do the right thing, which seems to have gotten you little more than a best friend who I think won’t be a best friend for much longer.

If only I hadn’t confessed to you.

By telling you his secret, he’s now made you complicit in his betrayal, and that’s a horrible situation to be in, especially when you’re around the boyfriend.

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

There is no victory here, no clear right path.

What seems right to me is to protect yourself. You will not lie on his behalf to his boyfriend, or to anyone else.

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

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