Dear Meredith,

I recently ended a relationship with a man I was seeing on and off for more than a year. We met at my workplace. When we first started dating, he had supposedly just ended a long-term relationship, so I proceeded with caution. He tended to waffle between wanting more from me and insisting that he was done with me. This was very confusing, and resulted in the first breakup when I pretty much ceased all contact.

Over the next several months, he initiated a few encounters, which led me to believe enough time had passed for us to be cordial again. One conversation led to another, and the next thing I knew, we had decided to give things one more chance. I was encouraged by how genuinely remorseful he was and how openly he expressed his feelings. I said I would take things at my own pace and would need clarification about past uncertainties. We both agreed to be more forthcoming and make time for the other when possible.

We had nice dates with endless conversation. He was much more attentive, even generous with gifts. While our communication had improved, I often felt pressured to move faster than I wanted to. Even though I grew more comfortable putting myself out there with him, he would question me often about whether I really wanted a relationship. In fact, it was shortly after we had become more intimate with each other that he quickly raised a lot of red flags. He frequently inquired about the gender of the friends I spent time with (he’d never done that before), telling me to “behave” when I went on a day trip to see old friends. It was a tiring cycle of explanations to reassure him that I wasn’t dissing him/losing interest, and his apologies.

I attempted to discuss and understand the reasons for this cycle when we met up to have the “where are we going” conversation (which HE planned). The evening ended with me ending the relationship for good. I realized that we are essentially incompatible due to different communication styles and attitudes about the nature of dating. Since then, I have also decided to end any friendship and communication outside of work, which I have clearly expressed in text message (and HE originally insisted on first). However, he continues to write long text messages that go between apologizing, to expressing how hurtful it was for me to just give up and keep the gifts he brought that evening since I “knew” I was ending things, back to doing anything for one more chance. My friends are encouraging me to block his number however, I am uncertain if I will need evidence for the future if anything should occur.

How should I handle this final breakup without potentially worsening the situation? Is there a gentler way for me to get him to stop without more extreme measures or language? If confronted at work or otherwise, what should I definitely say/do and not say/do so that we can both move on positively?

– Exhausted