originally published January 24, 2007

There’s a guy that I’ve been crushing on for like two years. So, he finally talks to me. He finally asks me out, and we have a great time. We have been inseparable since. Then the other night while we were in bed after we had sex, we had a big long talk about who we are and where we’re going and all that, and we talked a little about our pasts. He told me that he had slept with a hooker. Not recently or anything, but a few years ago. He said it was an accident, that he was drunk and he didn’t know she was a hooker. Is it weird that this freaks me out?

Naïve

Well, as long as he has been tested for STDs, I don’t see why this should be a deal breaker. I’m not sure I buy the “accident” thing, but he’s probably too embarrassed to admit it. And if you think about it, isn’t the fact that he trusts you enough to be honest with you about it a positive thing? You probably wouldn’t have ever found out if he hadn’t told you, and the fact that he did is probably saying good things about how he feels about you and where things are headed. Give the guy a break.

My boyfriend broke up with me a week ago. After dating a month, we decided to move in together. Looking back, it was way too soon. At the time though, we loved each other. It seemed like the right thing to do. He asked me to move in and I told him yes. He was the first one to say "I love you." We used to tell each other "I love you" several times a day. (Our relationship lasted three months, then he decided that we were on different paths. He said he would never want to marry me and didn’t want to date me. (His mom had given him her engagement ring, which I didn’t find out about until later.) I don’t understand what happened. We never argued or anything. Here’s the problem. We work together. I return to work in a week or so after taking some time off. How should I act? Should I ignore him unless I have to deal with him for something work-related? Should I try to be friends? I don’t hate him. I’m just hurt. This has been an emotional break up for me. I feel like I’ve lost my best friend.

Heartbroken

Did you break up in an ugly, slam-the-door-and-scream-obscenities kind of way? Or was it quietly sad, with both of you packing your stuff and wishing it had been different? The reason I ask is because like it or not, the tone of your last interaction has set the tone for your next one. If it was ugly, you’re going to have to confront him in a very calm and professional way, waving a white flag and telling him that despite whatever happened and everything that was said, you have to work together, and you’re both adults, and there can’t be drama. If it was calm and quiet, then you probably don’t need to have a big talk. You just have to let your actions speak for you. Be nice, but not too nice. You can’t exactly act like nothing ever happened, but you also shouldn’t dwell on it (at least not openly). Don’t go out of your way to ignore him (Childish! Tacky!), but don’t try too hard to be buddies with him, either. Just try to let things get back to normal as much as possible. It will take some time, but things will get easier. They always do. If you start to feel like you really can’t handle it, then get another job.

I'm extremely close to turning 30 and am NOT COOL WITH IT! I am nowhere near where I thought I would be at this age, so I've decided to go on a two-month adventure across the country and write a book about it before I turn 30 in April. I have a wish list of things that I want to accomplish in those two months and I've been building a network of people all over the United States that will help me. Am I nuts, do you feel that 30 is a "line in the sand" and you should be doing what you want by then?

Mike

Mike, I realize that this may be difficult for you to grasp, but there are a whole lot of people at many different ages who are “nowhere near” where they thought they would be at their current age. You know, things happen, relationships change, jobs suck, school doesn’t work out, you move, you travel, you get knocked up - whatever. Sometimes you just have to go with the flow. Are you crazy? Probably. But that’s okay, because as far as I can tell, we all are, and we’re way better off this way. The trip sounds like a great idea. Obviously you’re not doing too bad for your age if you can somehow afford to take two months off and travel and write. Good job. Go with it. As far as 30 being a “line in the sand," I would say that it is exactly that: an arbitrary line that will change when the wind blows. You are not very likely to wake up on your birthday feeling any different than you did the day before.

So my friend has just announced that she is going to marry her douchebag boyfriend. They haven’t been together that long, and I am pretty sure he is cheating on her. He cheated on his last girlfriend, and she knows that, but she thinks this is “totally different.” I heard the rumor from another person that would have no reason to lie to me about it. In fact, the other person doesn’t know him, but does know the person he is supposedly cheating with. Should I tell my friend? Should I try to verify the rumor? Should I keep my mouth shut? I don’t want her to get hurt, but I also don’t really want to get involved.

Ugh

Ugh, indeed. I know you’re trying to help, but there is no way in hell she’s going to thank you for sharing a nasty rumor about her loverboy. (An unsubstantiated one, no less!) As painful as it is, you’re going to have to let her find out on her own if this guy is a jackass. On the other hand, if you actually know he’s cheating, tell her immediately.

Jyl Inov

Got a question for Jyl? Submit your anonymous inquiry via the Reality Check form here.