Mentioning bad teeth may be worth the risk

Dear Lisi: I’ve been friends with this guy since we were teenagers. He’s really nice, sweet and fun to be around. Over the decade we’ve been friends, I’ve had a few boyfriends and now I’m in a serious relationship. He’s never been with anyone. And I think I know why.

He has the most unattractive teeth, discoloured and broken. And, though I know he brushes his teeth every morning and before bed, his breath isn’t pleasant most of the time. I always have gum on hand, and he appreciates when I give him some. He knows I love him as a friend and would do anything for him.

The problem is that his parents have the same unattractive teeth, so he doesn’t think it’s strange. But in our community, dental care is a normal routine thing for most people we know. And this isn’t about money because he could afford to do some basic dental work, even upscale work.

He recently lost his job and when he applied for another that he was perfect for, they gave the position to someone less capable. I honestly believe it’s a result of his teeth. He looks as though he has lived a much harder life than he has. I think people make assumptions based on his teeth. I want to tell him what I think. Should I?

Toothless Tales If you feel that what you will share will benefit him, then yes, I would tell your friend what’s on your mind. But be prepared that you may unintentionally hurt his feelings and it may affect your friendship. If you’re willing to take that risk, then talk to him honestly. If he can afford to get his teeth cleaned and fixed, even just the most basic that will enhance his appearance (and hopefully alter his bad breath), it’s worth the risk for him to have a better life.

FEEDBACK Regarding the boyfriend who is disorganized (April 5):

Reader — “It seems clear that the GF is an obsessive planner, while the boyfriend is the exact opposite. Neither is right or wrong — these are deep personality traits. The obsessive planners need this level of organization to feel safe/ relaxed/secure.

“Sadly, for those not like that, this level of organization creates unbelievable stress and pressure as each plan is felt as “goals that must be met”… so, this is just work, which leaves no area for spontaneity or real relaxation. The girlfriend’s demands are likely creating levels of stress within the boyfriend that she didn’t intend and has no clue about. He cannot “be like her” any more than a fish can gallop.

“They both need to realize and understand this about each other and find a way to satisfy each of their conflicting needs.

And for the planners out there, you cannot plan spontaneity.”