If your date has food stuck in their teeth, should you let them know? I think the answer depends on how long you’ve been dating. If I’ve been with someone for a while, I’d tell them right away. There’s a level of comfort you reach which leaves for less embarrassment. Though, I suppose I’d rationalize that my date was trying to save me from embarrassment if they let me know early on. My best friend and I usually ask each other to check each other’s teeth after we eat, so I think once you’re comfortable with someone it’s safe to mention. However if it’s a first date, I probably wouldn’t say anything to avoid leaving my date feeling embarrassed. The problem with being a somewhat socially awkward over-thinker is that I sit there wondering if I should say something every time they smile. Then, when they come back from the bathroom and it’s gone I think, “Oh no! They noticed it and took it out, which means they know I knew and didn’t say anything!” (That’s referring to my night out with the tourist girl.) Of course, there are probably numerous much more embarrassing things which could happen on a date. How long would you wait before letting your date know they had something stuck in their teeth?