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Boyfriend Gives His Teeth the BrushoffPrudie counsels a woman whose partner is lax at oral care—and other advice seekers.

Updated Tuesday, June 23, 2009, at 3:49 PM ET

Emily Yoffe: I've said before that I've often wished I could put together all the "attractive, smart, nice, accomplished" people who have somehow managed to get pretty far into adulthood without ever having a romantic relationship. You should start by asking your friends to have a blunt conversation with you as to why they think you've never connected with a guy. Is there something you're doing that they haven't wanted to mention to you? Beyond figuring out what signals you may be sending, you've got to work on not getting angry and bitter—that would make any potential partner flee. Keep trying, keep open, keep your expectations low, and ask your friends to help you connect with men who have expressed a desire to have a serious girlfriend.

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Philadelphia, Penn.: Two good friends of mine have been dating for about six months. I cheered on the relationship in the beginning, but am now wishing I had completely butted out. Friend #1 is head over heels in love with Friend #2, and is currently planning a cross-country move to be with her. In our phone conversations, he tells me how great she is, how he's in love with her, etc. Friend #2 is clearly not as interested. When we talk on the phone, she'll just say he seems "cool" and "pretty nice", and how he's "probably good for her" after the jerks she's dated. (A fiancé broke up with her two years ago). I honestly think she wants to like him, but it's pretty obvious that the feelings aren't there. I know I should stay out of their business, but the thought of Friend #1 uprooting his life to move to the West Coast is heartbreaking—especially since I'm pretty sure he wouldn't if he knew how lukewarmly she talked about him.

Emily Yoffe: This is your chance to completely butt out. They are both adults and it's up to Friends #1 and #2 to decide where they want to live and how they want to conduct their romantic lives.

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Philadelphia, Penn.: Hi Prudie, My husband and I just bought plane tickets to go see a friend's new baby in August. But my mother-in-law just informed me that she's having a big 60th birthday party for herself that weekend! She was really upset when she heard we'd be out of town, but changing the tickets will be hundreds of dollars. What should we do?

Emily Yoffe: You have to look at this in the longer term than the immediate cost. Is your mother-in-law's weekend absolutely set, or is she flexible? If it's set, you and your husband know if she's the kind of person who, after her initial upset, would say she understands she should have told your earlier, and she knows it will be too hard to change your travel plans, then you can go. But maybe she's the kind of person who will bring this up at her 70th, 80th, and 90th birthdays. If that's the case, amortize the cost of the tickets over those decades, and tell your friends you have to reschedule.

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Glendora, Calif.: Hi Emily.

I need a little workplace guidance. About once or twice a week, a male coworker will buy a coffee drink for myself and another female in the office. The gesture is very sweet and much appreciated. The problem is that neither I nor my female coworker like the drink he chooses for us. It feels like a waste of money for him to spend 3 or 4 dollars for each of us when we both inevitably pour the drinks down the drain.

What is the polite thing to do in this situation? Would it seem ungrateful to tell him what kind of drink I would prefer or should I just let him continue to spend his money in vain to spare his feelings?

Emily Yoffe: This guy is shelling out about $16 a week in unwanted gifts, so that's a lot of money to go down the drain. Also, picking up an occasional coffee, etc. for a colleague is one thing, but a constant stream of one-way gifts can be uncomfortable The two of you should tell him that while you very much appreciate his thoughtfulness, both of you are trying to cut down on snacks, and that the drinks are delicious but too caloric for you. Tell him that he's wonderfully generous, but your waistlines and his wallet would be in better shape if he cut back.

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Just overweight, thanks: Speaking of people asking if you're expecting a baby, is there way to say "no" that isn't awkward for them? It happened to me recently in a professional context, and I wasn't sure the best way to get past the moment.

Emily Yoffe: I think Dave Barry's rule is the best: Never ask a woman you're not sure is pregnant if she's pregnant, even if you notice a baby's head appears to be emerging from her. Yes, this is embarrassing for all concerned. So if you're the one being asked, you can laugh it off by saying, "I'm not. But if I were the fathers would be Ben & Jerry."

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Emily Yoffe: Thanks everyone. Talk to you next Monday.