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The Delicate Art of Dating Someone New While Still Grieving From a Breakup

·1305 words·7 mins
Advice Friend

Hi Page! Your writing has been such a source of community and inspiration for me, especially as someone fairly new to polyamory. I’m wondering: what is your experience with healing from a breakup while still in other romantic relationships? My long-term partner and I recently broke up. I started seeing someone else pretty shortly afterwards. Usually I’d wait for longer to give myself time to mourn and grieve, but the new relationship is in a polyamorous context, and began as more of a romantic friendship. Now, I don’t know how to give myself space to mourn and be sad without bringing that energy to my new relationship. Would love your thoughts, stories, and wisdom!


I know this feeling all too well. It brings me back to the web burning of 2011.

In the span of four months, I went through a series of breakups that ultimately ended four of my five current relationships. And as if that weren’t enough, one of those breakups was a divorce. A divorce that ended a relationship that had been going on for over a decade.

The breakups themselves were incredibly stressful. Everything felt shaky and uncertain. And the strangeness of the situation wasn’t helped at all by the fact that the fifth relationship was still going on. My heart had effectively been broken four times in quick succession, and yet here I was still dating someone. And Justin was someone who was relatively new (interestingly, we had spent about a year as a close romantic friendship ourselves before dating, similar to what you mention).

Complicating matters was the fact that my soon-to-be-ex husband Seth was actually living with Justin and me for a bit until Seth got some practical matters sorted out. Seth’s presence was incredibly stressful for Justin. Part of this was because Seth wasn’t the best roommate (he’s quite a bit messier than me, and I’m naturally messier than Justin). But part of it was also due to the tension between Seth and me in those final weeks of living together. Here’s how Justin put it in his journal at the time:

I hate watching her get hurt, and watching him continue to jab at her emotionally. He lashes out constantly, and can’t even admit that he does it.

Poor thing. That had to have been hard to watch.

Even after Seth left, there was quite a while that I was dealing with logistics surrounding the divorce. As part of that process, I went to counseling, which unearthed still more issues:

“What you’re realizing,” my therapist said, “is that he didn’t really love you.”

I protested, told her that he said it plenty.

“While he may have said he loved you, at the very least, when you both said ‘love,’ you and he were talking about very different things.”

Ouch. Right to the gut. It didn’t feel good to hear. But I knew on some level that she was right.

And that was why I was paying her, after all. I had plenty of friends. People in my life who I could talk to and feel good. I didn’t need that.

Sue had a different part to play. She was there to push me. Take me by the scruff of my neck, push me down on the ground, force me to smell my own bullshit. Like the dog who’s had the accident on the living room rug. It wasn’t pretty, but I needed to know what I was doing to myself so I could stop doing it.

Of course, it looked rather genteel in practice. She was often wearing pretty sweaters, sitting in a very relaxed position in a beautiful armchair of indeterminate age.

And we were usually both drinking tea.

But she still let the verbal punches fly. And she certainly wouldn’t let me get away with skirting past the painful parts. Or telling myself the same face-saving lies about people in my life who, truth be told, hadn’t exactly treated me all that well. At least not as well as I’d treated them.

She landed dozens of hits on me during the time we worked together.

And every time I got hit with a “punch” from my therapist, the impact was something I’d take home to Justin. Even if I didn’t discuss the issues raised in therapy directly with him, I was in effect taking that energy everywhere I went. Including into my relationship with him.


I checked in with Justin when I got this letter. Asked him the following questions:

  • From the perspective of the person who was partnered to the grieving person (me), could you tell that I was working through stuff?
  • Did you find it personally painful by proxy?
  • Do you think it affected our relationship and if so, positively, negatively, how, etc?

Justin replied that he wasn’t sure. That it was quite a while ago. That he remembers it being a bit stressful, especially when Seth lived with us. But he didn’t comment on the rest. Ultimately, he couldn’t be more specific in his recall of that time.

And while I was (as always) hoping for a juicier story,  his answer is probably a good sign. It’s probably for the best that he doesn’t have much more to say about what it was like to seriously date someone who was dealing with a bunch of breakups and ultimately a divorce. Was it difficult sometimes? Sure. But it’s part of our story now. My heartbreak and recovery from those events were folded into our relationship. A relationship which — by the way, I can say without hesitation  — is one of the best I’ve ever had.

And from my viewpoint, I’m eternally grateful to have had his support as I healed. Sometimes it felt like it was us against the world. But sitting here, seven years out from that terrible summer, it feels like we won.

And at the end of the day, while I never would have chosen to deal with all of that at once, I know for certain I have someone in my life who will be there for me during tough times.


Here’s some advice:

  • Remember that not everyone grieves the same way — and that when it comes to grief, basically any reaction is okay. There’s no “normal” here. Maybe you feel sad for longer than others would. Maybe you feel better faster. Either way, there’s no need to feel guilty about what your process is. Grief is very individual and can even be wildly different for the same person from event to event depending on what else is going on in your life.


  • The sad energy probably will cross over a bit into your relationship. I find that trying to keep energy 100% separate often does more harm than good. Mixing inevitably happens. What’s crucial is not letting it happen too much or letting that stray energy have a negative impact. As always, it’s important to do the best you can at  shifting gears. Here’s a post where I talk about some techniques that can help with that.


  • When it comes to accepting support from your partner, follow your partner’s lead and respect whatever boundaries they set. Justin actually took a very active role in helping me through my heartbreak (for example, it was his idea that I go to therapy in the first place). But there were definitely certain topics that he wasn’t comfortable discussing. So I accepted the help he freely offered while at the same time staying away from areas he wasn’t so wild about being involved in. What those will be will likely depend on who your partner is. What’s important is being sensitive and respectful.

Have a question about a post? Maybe need some advice about a relationship or situation? Write me. I love getting messages from you.


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