Just grin and bear it

Q 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.

But 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.

Where to Begin?

A 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 health issue, 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 lend him the money now.