Are these real red flags?

Hi Meredith,

I have been single for the past two years after ending a physically and verbally abusive relationship.

In the two years that I have been single, I made a concerted effort to work on myself as a person. I found a great therapist and took the time to learn about myself, what I want, what I can offer, and who I am. I can honestly say I feel more confident than I have in years, and recently landed a job I love and got my own place!

I was also lucky enough to meet a great guy a few weeks ago. We really hit it off and spend most of our free time together. I honestly love being around him. We share so many of the same ideals, hobbies, and humor. It's almost like he is the male version of me (which I think is fantastic!). I've never clicked with someone so quickly, or felt so safe and secure. He takes the time to build me up and point out my successes every chance he gets. But for as much I like him when I am with him, when I am away from him and have time to think, there are some things that don't sit well with me. He is very open about the fact that he was devastated when his last relationship ended, and a lot of our conversations always seem to end up back at him pointing out how he had wanted his ex to be more like me. This makes me feel jealous -- like he wishes it were her beside him, not me. Is that my own insecurity, or will I always fall short because I'm not her? On top of that he is unemployed, not as financially stable as I am, and has pretty terrible criminal record from when he was younger.

Am I selling myself short? Am I trying to make something work with someone who is clearly not over his ex? Should his past matter if I love the person that he is today? Or, at the end of the day, am I finding red flags and over analyzing them because I'm afraid to be in a relationship again?

– Overanalyzing in Watertown


These red flags seem legit to me, OIW. You're upset about his obsession with his ex, his "pretty terrible criminal record," and his financial instability. It's not like you're overreacting to him showing up late for a date.

It's pretty clear that you're not ready to walk away just yet, so please use this time with him to get your questions answered. Ask him to stop talking about his ex and see if he can respect your wishes. Also have a few more conversations about his past and how it will affect his future. Does he share your priorities? Does he have a plan?

My big piece of advice is to take things slow. Like, very slow. You barely know this man, so there's no need to turn him into a serious boyfriend. After just a few weeks, you're still figuring out what makes you happy. My guess is that after a few more dates these red flags will either shrink or grow. Maybe there will be new ones.

Just know that if you're having issues and asking questions, it's not because you're afraid to be in a relationship. It's because you're smart and capable. It's because you've learned to trust your gut. If your gut says walk away, you must follow orders. If you don't, you're selling yourself short. And please, keep your therapist and friends in the loop. You're not supposed to do this alone.

Readers? Criminal record? Ex? Male version of the letter writer? Should she walk away now or keep this going? Is she selling herself short? How can she slow this down? Help.

– Meredith