My boyfriend of six months has had a female best friend. She’s tried breaking us up countless times.

He would always vent to her over personal problems. He and I never really fought unless it was something stupid.

Then she started to talk about all of our secrets. It was getting to the point where breaking up was the answer, because we were always fighting.

He finally gave up on the friendship, by telling her, “If you can’t respect my relationship, we can’t be friends.”

He got me a ring. She actually stole it, and then gave it back.

After all this, he’s thinking of being friends again... it’s like he doesn’t care.

Should I dump him, even if I don’t want to?

Annoyed Girlfriend

This isn’t a “friendship,” it’s a drama that she looks for, and he feeds, just by talking to her.

She does NOT respect the relationship, or either of you as people. She may want him for herself, or just loves to stir up crises.

Either he dumps her, or you dump him.

I’m a man, separated for a year after a long marriage. I’m mid-60s, and for the last five years could no longer accept my wife’s choice for both of us to live in a boring, frightened way, waiting for some final illness to get us.

We’re both still healthy, and I still want to learn and do new things (I’m taking courses, re-joined a fitness club), love to travel, etc.

Now that I’m on my own, I also want to date. I enjoy the company of women and am easily enthused when I meet someone I like.

The problem I’m finding is that some women have felt I’ve led them on if I didn’t want to talk about the long-term future after just a few dates.

Dating after 25 years is more complicated than I thought, both from the online start and when you meet in person.

Should I be cooler even with women I’m attracted to, or be natural and move on if they expect more too soon? One woman talked about moving together after we’d been out twice!

Newbie on the Scene

It’s a balance – natural warmth is always better, so don’t be cool and distant, but don’t rush into a series of consecutive dates, weekends together, and other signals that you’re getting attached right away.

That’s what annoys women who are hoping for a lasting relationship and looking for those supposedly positive signs.

Be honest that you’re not that long separated, and not yet finally divorced. If you have adult children and grandchildren, then your personal life is complex, as are the lives of many women you’re likely to date.

This means that rushing into a steady thing may involve and affect several others in the other person’s life and your own… so go slow.

It’s all about truly getting to know someone, while not being unrealistic either positively or negatively. Also, it means seeing what areas would require compromise on your part, should you want the relationship to progress.

You can still show enthusiasm about enjoying time when you’re with someone, while also being clear that you have a separate meaningful life and are not needy of an instant commitment.

Share some of your new interests and see if the woman relates to them. Learn some of her interests, but also some of her quirks and tastes.

If you soon realize she’s not a long-term companion, then scale back to a friendship only, or move on.

My younger sister gets everything she wants, even now that we’re adults. My parents just bought her a car, something they never did for me. Their answer is that she has children, I don’t. But I could also have used the financial help.

How do I deal with this unfairness?

Always Treated Differently

There’s history here, as to how this dynamic developed… whether she was the much younger “baby,” had illnesses, or was just more demanding, which caused your parents to indulge her more.

If you’re unsure of the underlying reasons, you could ask your parents why they’ve always done this.

Or, you could accept that they recognized their grandchildren’s needs for their mother to have easy transportation.

That said, you could say why you need some financial help, too… if they can afford it.

Otherwise, be comfortable and proud that they probably see you as strong, competent, and independent.