Keep past in the past
Q: My boyfriend and I are very close and share everything with each other. Recently he asked me about my sexual history. I’ve done some pretty wild stuff in the past. Should I tell him about it? Or is it better to keep it on the down low?
Steve: That’s an easy one: No. And don’t ask him about his sexual past either. In other words, don’t ask, don’t tell. No upside on kissing and telling.
Mia: Tell your boyfriend? Men are insecure and petty, dear. Either he’ll be freaked out and feel inadequate or he’ll judge you harshly. Better to keep things in the past. But if you’d like to get the wild stuff off your chest, Steve and I are all ears (OK, maybe not Steve, his heart might not survive).
Q: I recently broke up with Mike, a guy I work with. It hasn’t been easy. Now Bob, another man I work with, wants to date me. I’m interested, but Mike is the jealous type. It’s uncomfortable enough without adding to the tension, but I am really attracted to Bob. What should I do?
Steve: Don’t get your lay where you get your pay. Office romances are inevitable but often a bad idea because you get a twofer when things go wrong: screwed-up personal life and screwed-up professional life. I’d advise seeking a man outside your workplace, but if you insist, be as discreet as possible or you, Bob and Mike will all wind up in the boss’s doghouse.
Mia: If you can be very secretive – that means no long lunches, no drinks in the bar across the street, definitely no making out in the men’s room – then you might be able to get away with dating Bob. My parents met at work, so I can’t totally bash workplace love. But be careful. It’s no fun being branded the office skank.
Q: My family is planning a big vacation in the Bahamas for next winter. My brothers are all bringing their wives and kids. Here’s my dilemma: Should I tell my girlfriend of six months about the trip and buy her a ticket, etc.? I’m just worried that it makes our relationship really serious, to be planning a trip six months ahead of time. I don’t know if I’m ready. Also, what if we break up between now and then? Then I’m out the money for her ticket. How should I handle this?
Steve: Assume the best, prepare for the worst. If, at this moment, you’d really enjoy her company, make the plans. But quietly purchase vacation insurance in case you have to cancel.
Mia: You don’t really need to book six months in advance anyway, so why not wait a couple of months and see how the relationship progresses? If you buy tickets now and then break up in July, you’ll feel pretty silly. Of course, I can think of a lot of women who would love a free trip to the Bahamas, so if ultimately you’re stuck with an extra ticket, maybe you can lure in some hot dates!