Hey Bonita,

Last semester, I made the worst mistake of my life about the best person I'd ever met. After being in two super-toxic relationships that sent me to therapy, I met a guy who I thought was literally perfect (inside and out, if you know what I mean). I got so swept off my feet by the first person who loved me for me that I ignored several red flags: He was very secretive about our relationship, I had to lie to his sister about being "just a friend" when we met, and he had wild mood swings from one day to the next that made it feel like I was trying to love two different people from one day to the next. 

After almost two semesters, he went through the worst depressive episode that I'd seen, and he broke up with me the weekend before Valentine's Day. But two weeks before he dumped me, I cheated on him. I couldn't make up my mind about whether I was strong enough to stick with his bipolar antics, and I let the frustration take action. We mutually agreed to block each other on literally everything after the breakup, so apologizing isn't even an option. 

Bonita, I can't forgive myself, and I don't know what to do. I've spent several months in denial, blaming him for the heartbreak and playing the victim in the relationship to repress my own guilt. Now that I've realized it, I feel like absolute shit. I've even asked God to forgive me, and I'm agnostic.

On top of that, I've been talking to this new guy all summer and decided I want to actually go on a date with him soon. He's handsome and a kind soul, and that makes me feel guilty, too. I don’t know whether I should tell him that I cheated in a past relationship—practically brand myself with a scarlet letter and have him probably lose interest in me—or keep it a secret and feel like I'm hiding stuff from someone who’s potentially long-term. 

How can I take responsibility for my actions but not beat myself up over it? Is it even possible to own the fact that I made the worst possible fuck-up in a relationship without letting it continue to make me feel like I'll never deserve love again? Last of all, for future reference, what should be a healthy policy for two people who are dating as far as when or if to talk about past relationships and mistakes that were made?

So, you feel awful about cheating. You feel so terrible that you’re asking yourself if you deserve love at all, and you even dipped back into a religion you don’t fully believe in. Your contrition is clear and powerful, and that’s more than I can say for anyone who ever personally did me dirty. Honestly, I think you’ve already taken responsibility by owning your bad behavior, letting yourself feel remorseful and shameful for it, going to therapy and (hopefully) vowing to never do something like that again. 

Do you feel like you need to express all of this to your ex in order to truly atone for your infidelity? I don’t recommend that, because he sounds unstable and unhealthy for you, and I worry that he’d react in a completely unhelpful way. (I also suspect he was cheating on you the entire time, since he wanted your relationship kept secret—a classic scumbag move.) Even scumbags deserve respect, but I don’t think it would be worth it to dredge up the past with someone whose behavior sent you to therapy. You don’t have to drag him into this to learn from this experience.

You deserve love, and you deserve second chances. We all do. Go on a date with that hottie and take it easy—it’s just a date. I think the cheating conversation should come up around the same time as the “What are we?” conversation, and you certainly wouldn’t rush into that kind of talk, would you? There is no need to pillory yourself over this. You messed up, homie, and you know it, and you’re taking steps to become a better person. I’m proud of you. I hope your date goes well.

Need advice? Email [email protected], use the anonymous form at flagpole.com/getadvice, or find Bonita on Twitter: @flagpolebonita.