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Neena, 31
What skills do lawyers possess that make them better lovers?
Attention to detail. And we do a lot of talking.
Are "love contracts" a good thing?
They're total horseshit. People will say, "Oh yeah, let's break it down," but one person is always going to be more involved than the other. And this is like a prenuptial agreement — you're assuming you're going to break up and that someone is not going to like the other person. Afterward, are you really going to sit there in a meeting and say, "No really, Bill, what do you think?" No. You're going to be like, "Fuck you, Bill. It doesn't happen to everyone, and you do have a small penis!"
 Is there a safe way for me to pursue my boss?
No, but it's always exciting.
How could a boss safely pursue someone who works for them?
Transfer the person to another department. It's always going to be terrible and end badly, but it will be the best sex they ever had.
When you drunkenly kiss a co-worker at a holiday party, how do you save face the next day?
Just bury your head in the sand. Ignore, ignore, ignore. Then they'll get pissed off and ask you out on a date.
Is it sexual harassment to ask an ambiguous colleague what their sexual preference is? Is it just rude? What's the best way to ask?
It's totally rude, but take them out for tequila. Be like, "So buddy, which way do you swing?" That way you can blame it on the tequila and have no legal liability.
Is that an official loophole?
No, but that way you can always back out of it — "Oh, I'm so sorry! How rude of me!"
What's the best way to get a lawyer to go home with you?
Don't make a lawyer joke.
Kate, 34
How can I recover from rumors that I've fucked my way to the top — particularly if they're true?
Be very good at your job.
I've been dating a coworker. I want to break things off. How can I do this without creating a hostile work environment? Should I come to terms with the fact that everyone at work will soon know my secrets?
Maybe. I would suggest breaking it off by saying you're not comfortable working together and dating. Then say, "I'd appreciate if you didn't tell people the nature of our chat." Turn it into a work-related breakup.
A new girl I like at work flirts with this dickhead who I know (through office gossip) has herpes. Should I tell her?
Absolutely not. It's generally a bad idea to feel confident that someone has an STD without having the test results in your hand. If it's not true, they could potentially sue you for slander. Of course, if it is true, it's not slander.
How much of your personal life is appropriate to reveal at work?
The fact that you have one. That's it. Of course, nobody ever follows that rule.
The new woman I'm seeing lives all the way across town from me. Short of quitting our jobs, how can we get some face time in during the week?
Try to do a date night where you meet in the middle somewhere. When my boyfriend and I weren't living together, we rarely saw each other during the week. I'd say establish a date night and nights where you stay at each other's houses.
What's the best way to get a lawyer to go home with you?
Get them really drunk.
Same as everyone else, it turns out.
Exactly. I mean that's the way lawyers do it to each other, so I imagine it could work for you.
Adam, 41
Is it sexual harassment to ask an ambiguous colleague what their sexual preference is? Is it just rude?
I'm not for this Puritanical shit. If you're relatively friendly with the person, you could do it, but I'm wondering what your motivation is in asking that question. If you think you know someone that person might like and just want to verify that they're into that gender, then it's okay. But if you're just trying to pry into someone's personal life, it's not cool.
I recently hooked up with a colleague. It fizzled out. Now another guy at that job is interested in me. Is it a bad idea to double-dip in the workplace?
Well — see, lawyers qualify things all the time — when you say it "fizzled out," it sounds like a mutual thing. So he probably wouldn't care who you dated. 
I've been dating a coworker. Now, though, I want to break it off. How can I do this without creating a hostile work environment? Should I come to terms with the fact that everyone at work will soon know my secrets?
Be direct. Speak to the person, tell them it's beyond your control. Say "I really like you, but I don't see this working out." You want people to be sympathetic and not feeling like you're manipulating them. So if you come out and say, "I don't want you to do this..." you're giving them power; they can use it as leverage that you spilled all this stuff. I think you just have to hope that the person is not a gossip.
Is there such a thing as an unhealthy amount of online dating?
Well, it's like dating in New York — you can serial-date very easily. There's always another hot-looking face or cool person out there. On some level, internet dating is an easy out for getting with one person. It's like eating a Twinkie. It's good, but I'm not sure how filling it is. Hopefully people realize there's more than that out there. As long as you're not obsessing over internet dating or doing it all the time, you'll be fine.
What's the procedure for staying friends with an ex? Are there certain rules that should always be followed?
I can think of only one ex I talk to now. This is going to sound boorish, but if you had a sexual relationship with some guy, then you just want to be friends, if he's still way into you . . . well, I would find that incredibly frustrating as a guy. Friendship is unrealistic unless he's moved on. And you've got to respect that.
What's the best way to get a lawyer to go home with you?
Ask them. For a chunk of my life I know I've missed obvious cues. A lot of it has to do with your own sense of self and sense of attractiveness to other people. So it's flattering, even if you're not into the person, if they're direct.
Jim, 32
Is there a safe way for me to pursue my boss?
Arrange it so that as few people know about it as possible. It should be between just you and your boss. It's been done.
How can I recover from rumors that I've fucked my way to the top — particularly if they're true?
Well, I guess you could just be a prude, but that would just suck if it wasn't natural. Just hang out with people. Give them a chance to get to know you, preferably not in situations where you could become drunk and flirtatious.
What's the rules for staying friends with an ex?
Make sure you tell your current girlfriend or wife. That's about it.
I'm dating multiple people. Should they know the others exist?
It depends. If you're really into them, be honest. But other than that, I wouldn't really say anything. I would want things to be natural. If I did eventually choose one partner, I would want to make that decision based on my impression of that person in their unaltered state. I wouldn't want them to put something on to compete.
My friend just started seeing a very smart, attractive woman. Only she's still in college. She's really mature, but he's 32 and leads a completely different lifestyle. Our other friends think it's awesome that he's dating this young chick, but I an only see potential for problems. Should I speak up so that at least he has balanced feedback besides "that's totally awesome"?
Yeah, you should speak up, but try to tone it down a bit. Don't try to impose your opinion on him. Just say, "Hey, are you sure about this? You know, she is a lot younger than you."
What advice question did I not ask that you think is worth asking?
What do you think of dating other attorneys?
What do you think about dating other attorneys?
I would avoid it if at all possible. This is based on my law-school experience: there was a lot of backstabbing, a lot of people going psychotic when stuff doesn't work out for them.
What's the best way to get a lawyer to go home with you?
"I tripped and fell in my apartment. I'm thinking of suing my landlord."
Interviews by Kate Sullivan. Sex Advice From... appears on Thursdays. Have questions for the general public? Send them to .
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