You've got bail
I am not attracted to "nice guys." I'm in my early 30s, and I don't think I have low self-esteem. I don't like to be mistreated, either. In fact, I want somebody loving and faithful, but I find the guys I "should" be dating predictable and boring. (So cliché, I know.) I seem to end up dating guys who cheat on me and have problems with the law. Is there such a thing as a good man who's also a bad boy? — Longing
When you date a "bad boy," there are always adjustments to be made, like getting adjusted to how he's sleeping with three of your friends.
It's easy to go unrealistic in looking for love. On the gooier side of romantic unrealism are the people determined to find their "soulmate." (No such perfect partner actually exists — just somebody they're compatible with in essential ways.) You, on the other hand, seem to be drawn to a guy who's had a cellmate.
Women very often go for bad boys out of low self-esteem, but you insist this isn't your problem. If not, maybe you aren't ready for a relationship and are going for guys who'll crash and burn what you have together before you get itchy to get out. But it seems more likely that you're an excitement junkie, turning to bad boys because they're reliable providers of it — the obvious downside being that they steal not only your heart but also your wall clock, which they sell to buy cigarettes.
Most people will tell you they like excitement, but chances are you have a strong aversion to the dull and routine and a craving for excitement and variety — to the point where your comfort zone is more the end of the bungee cord than the end of the couch. If you do feel this way, you're likely a high scorer in a personality trait that researcher Marvin Zuckerman deemed "sensation seeking," which involves a lust for novel, complex and intense sensations and experiences and a willingness to take physical and social risks to get them.
Sensation seeking appears to have a strong biological basis. So if this is part of your makeup, it's not like you can just decide to take up with the nearest accountant (that is, one who isn't embezzling from the mob). What you can do is look for good guys who have some of the positive qualities bad boys do, like confidence, charisma, creativity, spontaneity and a wicked sense of humor. They won't be easy to find, but consider that every bad boy you're with sets you back from getting together with a good guy who also meets your need for speed.
To keep yourself from taking any further dips in the felon pool, figure out alternative ways to get your excitement needs met (skydiving, tsunami-surfing, regular shortcuts through dark alleys?). This should free you up to meet the sort of guy who figures he's justified in using the carpool lane because he's pulling you behind his car on Rollerblades, not because he's got a couple of bank tellers tied up in the trunk.
Man of squeal
My brother has had a crush on this woman for a long time, but somehow the timing never worked out for them to date. A few months ago, I ran into her at a party. One thing led to another, and we ended up hooking up. Now my brother and this woman are finally giving it a go. He and I really don't have secrets from each other, so this is weighing on me, and I feel like I should tell him. — Need to Disclose
Having sex with a woman isn't like the moon landing. There's really no need to put the word out about who got there first. In general, when you lay a piece of information on someone, it should benefit them in some way. In this case, it would be one thing if you had important supplemental information to disclose, such as "sex with this woman is best followed up with a penicillin nightcap." But the disclosure you're looking to make simply self-serves a purpose — for you to get a load off your chest by immediately transferring it to your brother's.
What's done cannot be undone, and though some men can shrug off the sex their girlfriend had with some guy before they were dating, not all can, and it's especially hard when "some guy" is one they'll be seeing at every family gathering for the next 70-some years. Sure, as the saying goes, "information wants to be free." But as with a Great Dane in heat, that doesn't mean you should just open the gate and let it out ... so it can make sweet feverish love to everything in the neighborhood, starting with the neighbor's Mini Cooper.