I Have Lots of Doubts About a Great Guy. How Do I Decide Whether to Stay or Go?

I’m a 30-year-old straight woman. I was married at 21 and divorced at 28, then spent a bit of time on my own before meeting a man I really care for, but I’m uncertain how to face some decisions about the future. Here’s the data: we’ve been together 8 months. He is 36, kind and supportive toward me, extremely available, a therapist. Hilarious, deeply caring, gets my weird quirks, and the sex is incredible. He’s made it clear he wants a future with me. I adore him, and yet it feels like the list of things I would want to be different about him is too long. He often comes across as arrogant with others, which drives me NUTS. He can be an insufferable know-it-all. He is less financially responsible than me. Immature, in certain ways. Has ADHD and can’t seem to plan a date for us to save his life, even when I ask. He has a big personality, and I sometimes feel ‘small’ and less confident in his presence. Most of the activities we do together reflect his interests, which weirdly I have just started doing rather than suggesting my own activities for us. (Yes, I’m seeing a therapist.) He’s vegan and I’m not, and we’ve worked it out, but I wonder about what would happen if we had kids (which he has also said he is open to doing with me). Basically, I’m not sure if we have shared values. We don’t live together yet. I’m thinking of moving to a new city (I still live in my hometown and am desperate to get out). When I picture myself there, I don’t really see him with me. But I’m not sure why. Do I take the plunge and invite him? Or should I end it, because I’m a terrible asshole for having such overwhelming doubts about this basically great guy?  


On behalf of arrogant insufferable know-it-alls, you’re not a terrible asshole, Addie.

You’re just a woman who hasn’t met her husband yet. And that’s okay.

Ready for Lasting Love?
Ready for Lasting Love?

Your marriage took up your twenties. You certainly learned something from that.

Now, you’re in your first real post-marriage relationship and you’ve discovered that it’s…good, but not great.

This is the point where we need to distinguish between a great GUY and a great RELATIONSHIP.

This is the point where we need to distinguish between a great GUY and a great RELATIONSHIP.

For all I know, your hilarious, caring, sexy man IS a great guy, despite his flaws. But what I’m gathering from the tone of your email is that, as you’ve gotten to know him better over eight months, you’ve come to the unfortunate conclusion that he’s not a great guy for YOU.

Maybe he is for a day, a week, a month, or a year. But if you don’t see yourself with him long-term for whatever reason, that is some powerful data to pay attention to.

Listen, you ably articulated what you like and don’t like about this guy. No one — not even him — would be able to argue with your assessment.


Thus, it doesn’t matter if you feel like an asshole for passing him up and allowing him to condescend to another woman for the rest of his life; you’re doing the right thing.

Marriage isn’t about whether an individual guy is funny, kind, or great in bed, although, to be happy, you’ll have to get those needs met. Like I say in my free online training, marriage is basically about whether your respective puzzle pieces fit together seamlessly. From what you wrote, it sounds like there are a bunch of outstanding edges that are not meshing well, all which will drive you crazy if you ignore them now. I would tender the guess that you ignored a lot of things in your marriage as well.

Marriage is basically about whether your respective puzzle pieces fit together seamlessly.

Trust your gut, leave the guy, move to your new city, and find someone who makes you feel like the best version of yourself. When you do, I promise, you won’t need to write to a dating coach for guidance on what to do next.