Should I Be Worried That My New Boyfriend Admits to Being a Cad?

I have been dating a new guy, 40, for four months. So far, we really like each other. Not infrequently, though, he drops little warnings about his behavior in past relationships: He acknowledges a pattern of dropping women after he gets them to like him, for instance, and ending relationships because he feels trapped. His own father asked him if he had “messed up” our relationship yet. On the one hand, I’m glad we’re able to have these conversations, but on the other, I’m worried about moving forward with someone who has these patterns of behavior. Help!

ANXIOUS GIRLFRIEND

Hard truth: Just because your boyfriend owns up to his bad behavior in prior relationships doesn’t mean he is going to do any better with you. It is infinitely easier to identify patterns of crummy behavior than it is to change them. He may simply be insulating himself against your anger when he eventually pulls the same stunts with you. (“I told you what I’m like!”)

Still, there is no reason to conduct your love life based on my hunches. The next time your boyfriend refers to his history of falling short with women, ask him directly: “So, what’s your plan for a different outcome with me?” If he has one, be all ears! In my 30s, I worked really hard with a therapist to stop sabotaging my romantic relationships. Your boyfriend may be working on his issues, too.

But if he is simply repeating the same old moves, there isn’t much reason to hope for a better result here. In your position, I would talk to him about this, not wait around anxiously. Part of your job in a relationship is to look out for yourself, and this guy clearly has some remedial work to do before he is relationship-ready. You may as well ask him if he’s doing it.

Keeping Travel Headaches in Perspective

My friend and I are scheduled to leave in two weeks for a vacation in Asia. We booked it with a company that plans adventure travel for small groups. I’ve gone on many trips with them, on my own and with friends, and I’ve enjoyed them. The problem: My friend’s father died three weeks ago. I’ve texted her and sent a condolence card, but I haven’t heard back. I’m worried that she may not want to go on this trip, and while I want to give her space, I need to know. Full disclosure: She canceled on me at the last minute before a trip 10 years ago. So, I’m feeling especially annoyed that I deferred to her on issues like leaving from an inconvenient airport, and travel dates. Advice?