I’ve started dating a terrific woman who’s very pretty, and has a good figure. We get along well and she’s also sporty, so we do a lot of activities together.

However, she’s 36 and going gray early. She doesn’t seem to care, and I admire her for that. Yet she looks older than she is.

I’m 35 and still have a full head of dark hair. I keep fit and have been proud of my still-youthful looks, as I’m in a media field where it matters, no matter whether one likes that fact.

I already noticed one of my friends looking at my date quizzically, and he later asked me her age.

I’m impressed that she doesn’t mention the graying or even laugh it off. I don’t want to care either. But she does look as if she’s at least five or more years older.

I like this woman a lot. Would I be risking too much to talk to her about considering putting in some colour to cover the gray?

Gray Matter

Say nothing. Not if you want to get to know her better.

Any comment would have you sounding like a man trying to turn a real, confident, down-to-earth woman into arm-candy for your benefit.

Enjoy the dating, and if you develop stronger feelings for her, build the relationship on mutual respect, not on trying to re-shape her in your image.

Meanwhile, get a grip on your own self-image. No matter the field you’re in, what matters most is your own talents and competence at it, plus your self-respect doing the job.

If you actually have to judge the woman you like, according to false standards related to impressing colleagues and friends, then you’re not a very secure guy.

In which case, this self-assured woman is likely to drop you.

I’d dated a widower for three months and it took 16 dates before he stopped mentioning his late wife’s name.

I found that pretty unusual since she’d passed away eight years prior and he’s had a few relationships since then.

He’d text me every day, sometimes ask me to meet him for lunch (we work in the same general area), and he’d message me again at night.

We had dinners out, he took me to a play, we went to a jazz club, and attended a party together with mutual friends.

He was warm and interested in me conversationally, but made no move to get intimate until our last date.

When I didn’t hear from him for another week, I called him while he was spending the weekend with his son.

He was cold and dismissive. The message was clear that whatever we had was over.

That was six months ago but I keep wondering, what was that all about?

Still Feeling Rejected

It clearly was NOT anything negative about you.

Those dates and daily messaging were evidence of his sustained interest in you at the time.

But he’s obviously a complicated man, still dealing with the loss of his wife, making attempts at relationships, moving on when anyone feels close.

He isolates his connection with his son, not allowing any intrusions.

It indicates that he’s not prepared to develop any relationship into a long-term partnership - not the women before you, not you, and likely no one for years ahead.

Move on. He did you a favour, because any expectation of things getting more serious would’ve become an ongoing frustration.

This is about him, not you.

Our sister, who was single until 40, married an older man who had two adult children with kids of their own. She took on helping with his business, while still working, too.

Unfortunately, her husband turned out to have poor health.

She then looked after him at home, and often invited over his whole family to be with him, until the day he died.

To our surprise, his family rewarded her well by staying in close touch.

They respect all she did for their father and include her as their “stepmom.”

My brother and I hadn’t stayed that involved with our sister while we were raising our kids and she’d remained single.

But we’ve learned a lot from these welcoming, loyal “step-children” who consider her important to their family.

We’ve learned the importance of opening your heart to anyone in your life who shows decency and kindness as our sister did.