DEAR JANE: I’m so ashamed to admit it, but I only sleep with men who remind me of my aging father

Dear Jane,

I am 22 years old and work as a waitress at an upscale restaurant in New York City. I’m used to men hitting on me at work, but I usually politely turn them down because the thought of dating a client makes me uncomfortable.

That was until recently.

Last month a very handsome man entered the restaurant for a business dinner with a large group of people. He was very polite during their visit, even if some of the other guests in his group got a little too drunk and rowdy.

At the end of the meal he came up to me and told me that he thought I was very beautiful, and that he would like to take me on a date.

I couldn’t tell exactly how old this man was, but he was definitely a silver fox. I decided to say yes and thought, ‘What’s the big deal, it’s just dinner.’

That weekend he took me to a great bar, followed by a delicious dinner and then invited me to his huge apartment for a nightcap. I was so attracted to him and was pleasantly surprised by how sweet he was. We ended up sleeping together.

The next morning he made me breakfast and I joked that he sure knows how to treat a girl. He admitted that he was previously married and has two daughters. I was a bit shocked and asked how old he was. He said 63. I was stunned.

Not only is he almost three times my age, but he is also the same age as my own father.

Even though we had a great night, we didn’t see each other again (he never called), which was disappointing because I really enjoyed our time together.

But men my own age continually disappoint me with their immaturity, lack of style and… small apartments! So, looking for the same thrill, the next time an older man asked me out during my shift, I said yes.

I also enjoyed a great date with him and ended up staying the night, and again, it was great.

The downside is that I’m quite ashamed of myself. After all, I can’t have a ‘real future’ with a man the same age as my father. If we had a baby when I was 30… he’d be over 70!

But I also don’t know if I can date ‘kids’ again. Would it be so bad to consider a serious relationship with a much older man?

By,

Silver Fox Hunter

Dear Silver Fox Hunter,

I know couples with a big age difference, who have been together for years and are very happy. I also know couples with no age difference who start off strong but end up in relationship problems as they get older. There is no magic combination that guarantees successful collaboration, but there is a kind of ‘rule of thumb’.

When women in their 40s get together with partners in their 60s, problems often arise. At forty, many women are just reaching their peak, discovering who they are, feeling comfortable in their own skin and ready to take on the world. But at age 60, men often slow down and look forward to quiet nights and time at home. That can create a dysfunctional mix of priorities.

That said, I can’t tell you who you’re attracted to. Normally, women don’t demand enough from relationships – and we accept emotional immaturity from our partners. It looks like you don’t, so that’s a good start. But you should consider the specific qualities you find attractive in older men; perhaps this appeal has less to do with age and more to do with stage.

Wisdom and maturity are found in people in their twenties, just as stupidity and immaturity are found in people in their fifties. There are plenty of young men who are mature, sensible, have steady jobs and may be able to provide you with the stability and security you are looking for. So look for the person, not the number of years.

As for the small apartments, my advice is this: never rely on a man to give you the things you want. You are young and may have an entry-level job. Instead of spending your time hoping to meet a rich man, focus your energy on finding work that will bring you joy. What are you passionate about? How could you make a difference in the world?

When we are happy and fulfilled in our work, money often follows. Design your life instead of looking for someone to hand it over to you.

Dear Jane,

My wife and I have always had a wonderful friendship with my old college roommate and his wonderful wife.

We have known each other for more than 20 years. As young couples (before we all got married) we would hang out on the weekends, go on vacation together and talk about our lives.

We’ve seen each other’s good, bad and ugly – and nothing has ever come between us.

Now something is different.

Our friends have two children; a boy of ten and a girl of three. We have children the same age and spending time together as a family is a complete nightmare.

Their children act like monsters. The older boy is super aggressive and doesn’t know how to share. The little girl is a snotty diva who constantly throws hissy fits about nothing.

They even make trouble with my kids, who usually get along with almost everyone.

Moreover, our friends do not know how to parent. They refuse to discipline their children, even when it is clear that something needs to be done. Instead, they laugh it off.

One time I tried to tell my friend that he better get control of his little kids and their little problems before they became bigger kids… with bigger problems. But he got super cold, and since then his wife has been acting different towards me.

I would say we should just get together when someone else is watching the kids – but everyone is so busy we would never see them.

I feel like their kids ruined our friendship. What can I do?

By,

Frank Friend

Dear Frankfriend,

Oh, how my heart goes out to you. I still remember the times I watched in horror as the children of people I loved behaved in ways that I hated.

There was a time when our best friends’ teenage sons came over for Thanksgiving and the boys would sit at the table for the entire meal and play video games loudly, not talking to the other kids or anyone else.

And then there was the child who got up from the table and ran across the furniture, breaking a vase I cherished.

The stories are countless. Now that my own four children are grown and flown, thankfully I no longer have to deal with someone else’s clumsy children. But the experience taught me a valuable lesson: There is absolutely nothing anyone can do to change their friends’ children. So don’t try it. The kids didn’t ruin your friendship, but your unsolicited parenting advice might.

College roommates are special. They knew us before we even knew ourselves and before we started transforming into who we thought we were supposed to be as adults. They know – and love – the pure essence of you, just as you love them. That is an irreplaceable bond. You will make new friends, but old friends should be cherished. Don’t jeopardize that.

The very best solution is to accept that everyone parenting is different. It may not be your way, but it’s not your children either.

If your friends suggest getting together as a family, you can say that you would rather leave the kids at home and go out. If either of you can find someone to watch the kids, so be it. Just tell them the plans aren’t working for you.

If this friendship is important to you, the only way is to wait out these very intense parenting years. You may need to find alternative ways to socialize. Perhaps this relationship is maintained through phone calls and Zoom chats. As difficult as it may sound, the friendship will have to be put on the back burner for the time being.

If you want this friendship to survive, reserve your judgment about their parenting and their children.