I began dating a friend of mine after knowing him for several years. The relationship is wonderful.

He’s caring and attentive, and my champion. He’s the person with whom I want to spend my life.

However, I find it hard not to notice that his teeth are very discoloured and need some serious dentistry to fix multiple chips and other issues.

It's very noticeable in his smile, distracting when speaking to him, and something that I’m a bit embarrassed by.
I have the funds to be able to pay for him to fix his smile. But I don't know if I should, or how to even approach the subject with him.

Where to Begin?

Begin with the sensitivity that you already recognize is needed.

That means NOT mentioning that you’re embarrassed by his appearance, which is what a “smile” first shows.

You’d make him far too uncomfortable and likely hurt too.

It also means not offering to pay to “fix” him. That’s how he might feel about your doing so, even though it’s only about dental work and generous.

No, the best approach is to somehow raise the topic of teeth one day – perhaps as a healthy topic, or an anecdote from your youth – not about him, specifically.

If he shows interest in hoping to have dental work done someday, that’s when you can offer to loan him the money now, since cared-for teeth are important to overall health.

FEEDBACK Regarding the man whose wife of four years is a “chronic manipulator” (Feb. 16):

Reader – “I felt many of the things this man has experienced, while in a toxic relationship.

“Getting out from the relationship will improve many of them… in time.

“I’m 48, dated her off and on for five years. She helped me through a nasty dark divorce.

“I was to move in eight months ago. I helped pay for her house renovations with the understanding that my contribution is returned if the relationship terminated.

“We drafted a cohabitation agreement but didn’t sign it.

“She was extremely controlling and volatile, always blaming me for any issue. I left the relationship three weeks before the moving date.

“She threatened that if I entered the house to retrieve any belongings I’d be charged. She changed the passcode on locks, told me to get a lawyer, and wouldn’t pay me anything.

“I offered to pay for a mediator of her choosing. She refused.

“I had police attend with me to attempt to remove my property. She came out of the house drunk and screamed at two officers and myself and refused entry.

“Later, the police called me and said she’d complained. I was to stay away from her, her house, and have no contact other than through lawyers.

“We eventually settled out of court. She’s paying back a portion of the money and I’m out $20,000.

“She owns the house, has a six-figure salary, yet wanted me to pay 70% of all household expenses.

“I have a good income but her children are at the house much more than mine would’ve been. She has her master’s degree and a great career, but she sucked as a partner.

“I now have calm in my life.

“The writer’s wife will do many of these same things. He should get out now while he can. She won’t change.

“He’ll go through hell for awhile but there is light at the end of the tunnel.”

 Ellie – Warning to men and women: Be alert to a partner’s personality red flags before making serious commitments.

FEEDBACK About the husband with phobias including going to hospitals and doctors (Feb. 15 and Jan. 22):

Reader – “It might be helpful to know that counselling is also available entirely by phone from therapists focused on this method of connecting.

“There’s a cost but it avoids many pitfalls that make going to a counsellor – distance, means of transportation, and phobias – seem impossible for so many.

“Otherwise, how does someone get effective counselling if it's almost impossible psychologically for that person to leave the house?

“The phone-in system can help deal with issues and maybe get someone to the point where they can get out and about.

“Then they can hopefully access other avenues of support.”

Ellie – An excellent reminder of phone and online counselling services, especially where there are multiple phobias.

In case mentioned, these also included going for a walk, new locations, open spaces, heights, flying, and feeling trapped in crowds.