Dear Wendy: “My Husband Won’t Stop Bragging About His Package”

It’s time again for “Shortcuts.” For every question, I’ll give my advice in two sentences or less, because sometimes the answer to a person’s question is so obvious and the need to hear it so great, being as clear and frank as possible is simply the best way to go. Today we discuss braggart husbands, commitment-phobe boyfriends, “test-driving” relationships, and what to do with a cigar box of memories.

My husband was fortunate to retire at the age of 50. We realized early on that discussing this with our friends created jealousy and resentment so agreed not to talk about it in any specific terms in public. Lately, I keep hearing my husband bragging about what a great package he got and how he is set and doesn’t have to work. I am sensitive to the fact that many of our friends are hurting financially and won’t be able to retire for many years. I have asked him to stop and he agrees, but then I hear him again at the next social gathering. What can I do to make it clear that his retirement terms are private and that he is ticking people off? — Embarrassed Retiree’s Wife

Tell him that the next time you hear him bragging about how great his package is, you’re going to correct him and tell everyone that his package isn’t quite as big as he’d like to think. I bet you never hear another peep out of him about it.

My boyfriend and I have been together almost three years now. I have no intention of pressuring him into marriage, but he is totally against talking about our future. It’s hard enough to make plans three months from now, so our future together seems pretty much off limits. I had a moment of weakness a couple of weeks ago and asked him how he saw the next few years spanning out. And he responded that he planned to “test drive” me for a few more years. It really hurt my feelings. I cover over 50 percent of our expenses, so now I feel used and I’m not sure how to proceed from here. — Confused Modern Woman

If after three years of “test driving,” he’s still unsure, there’s something wrong with the driver, not the car. It’s time for you to test drive being single.

Around two and half years ago, I ended a three and half year relationship with my first love (and live in boyfriend). I’ve gotten rid of most of my mementos of the relationship, except for this one cigar box filled with photos and a few letters. The thing is, I have absolutely no desire to keep the box. I’m not in contact with my ex, I doubt I’ll ever see him again, and frankly, the relationship has kind of haunted me (we were too serious too young, co-dependent, and had a horrendous break up) and the box brings back bad memories and regrets for me. However, basically all of my friends are telling me that I should just put the box up in the attic because “someday” I’ll want to go through and relive the memories. Do you think I should throw the box out or listen to my friends because someday I may regret tossing it? — Ms. Tidy

Nothing in your letter indicates your relationship was one you’d like to relive one day, but if you think there’s a small chance your friends might be right, you could always bury the cigar box in your yard or some place not too far away. Then, you get the closure of putting the relationship “in the ground,” but can always dig it back up if you feel a sudden pang of nostalgia (but my guess is you won’t).

I’ve been seeing a man once or more a week for about two months now and I’m a little confused about him. He says that he isn’t seeing anyone else but has mentioned that that’s mainly because he doesn’t have time to date more than one person. We also tend to have two types of “dates”: one where we stay in and he’s really affectionate and well … amazing (if you catch my drift), and the other where we go out to the movies or dinner and it seems as if we’re just friends. There’s no hand-holding, no touching, no arm-around-the-shoulder cuteness, and not even a kiss goodnight! Recently, he even asked for advice on buying a female friend of his a designer purse because she’s been having a “tough time lately.” Might I add, he’s a bit strapped for cash at the moment, but willing to pay for a designer (although from the outlet) purse. What gives?? Am I just a FWB? — Confused


Follow me on Twitter and get relationship tips and updates on new Dear Wendy columns!

*If you have a relationship/dating question I can help answer, send me your letters at {encode=”[email protected]” title=”[email protected]”}.