Dear Prudence: I'm a single woman in my 30s. I met a guy a couple of months ago through an online dating website, and we hit it off and are spending a lot of time together.

He is funny, smart, articulate, sensitive, talented and seems to adore me. The catch is that he is missing several of his teeth. In the front. This completely threw me off on our first date (his profile pictures all featured closed-mouth smiles, obviously). But I kept seeing him because we got along so well.

Now we're on the brink of entering a committed relationship. He has already introduced me to many of his friends and family members. My parents and most of my friends live in another state and, frankly, I would be embarrassed to introduce him to them because of his dental situation. He is in college and works part time, so I assume he doesn't have health insurance.

I would temporarily go into debt to fill in any holes in my mouth if I had them, but obviously this isn't a priority for him. I need some perspective on whether this is something worth feeling hesitant about. I don't know if I should even broach the subject with him.

How would I suggest he consider cosmetic dentistry? We've been very open and honest in our communication on other sticky matters, but I just don't know if I can go there. Please help!

Prudence says: Many people upon realizing a date was missing his front teeth would consider this a bridge too far. This guy must have some personality chops if you were won over by what came out of his mouth instead of being put off by what was missing from it.

As wonderful as he is, I'm chewing over how you could consider a serious relationship when you're too uncomfortable to bring up his dental condition and too embarrassed to have him meet your family. That's quite a gap in what most people would feel is the kind of emotional intimacy necessary for commitment.

You have to talk to him about his missing teeth, which will be awkward, but might also come as a relief to him since he's probably been wondering when you were going to mention it. Be direct and sympathetic. Say you think he's great, but that because of his dental issues, people are going to make unfair judgments about him, particularly once he starts looking for full-time work. Say you don't want people to fixate on something that's fixable. Explain that you know getting a partial denture or a more permanent solution is expensive, but give him this list of resources for finding affordable dental care.

If he lives within a reasonable distance of a dental school, he should look into being a guinea pig for a (supervised) dental student. It's a shame that privation and dental maladies are so closely linked. But moving ahead professionally — and personally — requires that your guy address this.