He was someone else’s nightmare

Hey Meredith,

I'm in a bit of a pickle here. The good news is I'm in love. Like, butterflies in the stomach, "Princess Diaries" leg-pop in love. My boyfriend is a precious angel of a man who once jumped off his skateboard to kiss me on the sidewalk of Mass. Ave, and I couldn't be happier with him. The bad news is he's got history. A month before we started hanging out, his last girlfriend kicked him to the curb for cheating on her with three different girls, one being her best friend. He's notorious for being this girl's nightmare ex-boyfriend who was manipulative, explosive, and lacked self-control.

At first, I was reluctant to get involved. My love life thus far had been enough of a mess, and the last thing I wanted was to date yet another walking red flag. But alas, the heart wants what it wants, and to the dismay of pretty much everyone in my life, I became his exclusive girlfriend after four months of casually dating. Things so far have been so good. He's thoughtful, caring, and communicative, and I'm very much surprised that things are going this well. Though I'm trying my best to let the relationship run its course, I have no idea how to navigate the issue of trust. Is it naive of me to think I'm any different than the last girl? Should I keep myself from getting comfortable to protect my heart in case something happens? I'm prepared to make the jump for this guy because I love the [expletive] out of him. I almost don't care if I get hurt. Am I being reckless? Help me, Boston Globe Love Letters. You're my only hope.

– Disaster Junkie


We're missing some information here. Perhaps you are, too.

Nowhere in this letter do you tell us how this man feels about his past relationship. Is he sorry about how he treated his ex-girlfriend? Does he say the stories about him are true? Has he changed? Does he care about any of this? Have you asked any of these questions?

It's easier to trust someone when you know how they learn from experiences and what they value. It kind of sounds like you have no idea whether your boyfriend is truly a "precious angel of a man" because you haven't had the awkward talks about what your lives were like before you found each other. It’s time to find out. Because it's not about whether you're any different than the last girl, it's about whether he's different this time around.

I don't believe that cheaters aways cheat and that this is doomed because of his history. I do believe people can grow and learn. But there has to be some self-reflection. People have to want to do better.

You sound very smitten with this man – it's OK to enjoy that! – but you can't ignore these doubts forever. Talk. Ask. Evaluate. Fill in the gaps.

– Meredith

Readers? Thoughts on these red flags?