Baggage Check: Tiger's Hit More Relationships Into the Rough

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I AM SOOOOOO IRRITATED with my boyfriend. Ever since this Tiger Woods stuff came out, we've been bickering. His first comments were about how stupid Tiger Woods was to get caught via cell phone. I told him that, clearly, Tiger Woods has issues and maybe he wanted to get caught. But his comments bother me, because I feel like he should be saying how much of a dog Tiger is, and instead he seems to think that he's just dumb for not being careful. It's like he doesn't think it's wrong to cheat. I find myself wondering whether he's not being honest with me, and how I'd ever know if he's so good at covering up. — Worried

These concerns need to be aired in a real conversation, not just a symbolic spat about a dude who chases birdies. Be honest. "You know, your comment about Tiger Woods' being stupid to get caught — it's been bothering me, because it makes me wonder whether you think that was the worst part of his actions." Perhaps it was a throwaway, ill-advised remark that he's now annoyed that you're dwelling on, and the spats are coming not from substance but from impatience and frustration. Or, there might be other signs that your boyfriend doesn't exactly believe in monogamy or honesty. For your own sake, try not to dwell on one reaction. Have a relaxed, patient conversation in which you get to the root of what's bothering you — emphasizing your overall concerns and not his comments.

Don't Wanna Put A Ring on It?
My girlfriend and I are going on a Caribbean vacation. I'm looking forward to it, but I think she might be expecting me to propose during this trip. (A buddy's wife and my girlfriend are close friends, and something seems to have been said about her hopes or expectations.) I have no intention of doing so — I'm just not near that at all yet. Now I want to send some sort of smoke signals out for her to not get her hopes up. I don't want to spend this whole trip feeling guilty for her anticipation. — Ugh

To my knowledge, Hallmark has not yet manufactured a line of "By the way, I'm not proposing!" greeting cards (Perhaps with a nice tissue paper inlay? Hey, I might be on to something!), so, clearly, there's no easy answer here.

But first, assess whether it's really certain that she's expecting something. Has she given you any indication that she expects a proposal, decent or indecent? And, more important, have you two actually discussed your future? If you're positive that your not proposing will ruin her trip, then go ahead and do it (kidding!). But you must have a direct, loving conversation — allow several days before your flight, and be as honest and transparent as possible.

Now's not the time to play coy, lest she think that's part of some secret question-popping strategy.

Talk back to Dr. Andrea by leaving a comment below. To ask a question for Baggage Check in the Express print edition, e-mail baggage@readexpress.com or submit an anonymous question here.

Art by Ben Claassen III for Express