Trying to overcome a complex dating history

Q: After divorce from a brief first marriage (no kids), I was with my second wife for 12 years and close with her two children. I knew that she’d had a whirlwind long-distance romance in between.

Two years ago, I heard from a mutual friend that my wife’s former lover was in town. I noted that my wife didn’t mention anything about him and went to an after-work meeting with my boss.

When I returned home around 11 p.m., my wife wasn’t home. I waited the next morning and when she returned around noon, I asked directly what she was going to do.

She said, “I’m not giving him up while he’s here.”

I said, “I’m gone.”

I packed, stayed with a friend and soon rented my own place. But I have remained closely in touch with the kids who are young adults now.

My question’s related to the opening up of socializing and dating.

I’m a healthy man of 52 who would like to find a partner I can love and trust.

I understand that most women in the appropriate age bracket for me probably also have complex histories.

What’s your advice for a decent guy who’s uncertain about how to get it right the third time around? Hopeful but Hesitant

A: Like many important goals, they’re best reached one step at a time.

Whether you meet someone through a dating site or a friend’s setup, get to know who a woman is as a person, not a potential mate.

Dating should be less about ticking off the boxes about your “ideal” partner, and more about learning her character, the people she cares about, the things that make her laugh and cry.

Finding similar interests is part of the search, but remember you can only play golf for so long. It’s an activity, not a character trait.

Your relationship history shows that you’re a resilient guy, and your connection to “former” stepchildren proves your decency.

Put one foot ahead of the other and start dating. You’ll do fine.

Q: My brother and I live in the same city, we’re both in our late 30s. I’m single, he’s married. I’m not fond of his wife and don’t relate to her but keep my feelings to myself.

Also, I’m not good with my brother’s three kids, age seven and younger. I just can’t get down to their level.

It has led to my brother and I becoming less close over the years. And I heard through the gossip mill that he thinks I don’t like him, which isn’t true. We were always good friends growing up.

What should I do?

The Single Brother

A: You don’t have to love a sister-inlaw, but you do have to try to maintain a respectful relationship.

You may not have said anything about your feelings for his wife, but your body language and verbal responses to her are likely obvious to both of them.

As for their young children, your distance (and your personal excuse for it) has been your bigger mistake. Kids love things to do, they need physical activity and mental stimulation, and parents are always looking for new ways to provide these.

Enter the beloved relative who’s gone to a children’s toy store, talked to a salesperson, confided lack of knowledge and bought the toy-car track, music box, colouring books and washable crayons, etc.

You don’t have to spend the whole visit on your knees, but a few minutes of it would help the kids actually see and appreciate you.

Ellie’s tip of the day

Learn someone’s character one insight at a time.