The first man I gave my number to after being widowed was a half-drunk traveler to the U.S. who wasn’t sure how to get to his Brooklyn apartment.

“Uber should be able to get me home,” he said, stepping off the high-end luxury yacht we had been on for the past six hours.

My girlfriend was with me, and it didn’t seem like a half-bad idea. We chatted with him for a while, met two of his friends, and I looked him up on Google to make sure his profession matched what he said. (It did, by the way.)

We parted, he said he’d reach out, and I contemplated the idea of what I had done as we ventured toward the closest NYC subway.

Give a drunk, random dude my number? Since when? (I later found out, through therapy and bereaved friends, that making bad relationship choices after grief is normal but, as a disclaimer, not encouraged.) Making bad relationship choices after grief is normal but, as a disclaimer, not encouraged. Click To Tweet

My girlfriend was good company and raved about the great time we had. She talked about the boat and the music and the food and the people and “that handsome guy you met.”

“He seemed decent,” she said as we walked down the subway steps which, in July, felt like voluntarily descending into hell. When we arrived at the bottom, I glanced over at the wooden bench, sat down, and mentally named the scenery.

Dirty, gray-slated subway cars. A few large rats. Random lady using the garbage lid as an eating tray. I tried to name it all. If I’m honest, I wasn’t spacey because of the alcohol. I needed a distraction.

“Are you even ready to date?” my friend asked me, whipping her brown and green tinted hair off her face. I hesitated and she gave me that if you lie, I’ll know look.

“I was thinking about that.” My head started see-sawing, trying to balance the idea of loving a man who had died while being open to loving a man who is living.

” … trying to balance the idea of loving a man who had died while being open to loving a man who is living.”

She and I chatted about loss and grief, and she asked me to refresh her brain on how long it had been, what I was feeling, and even how JR died, since I had never told her. Which I still didn’t, but talking about it with her gave me a fair assessment of whether I was ready – and I wasn’t.

The drunk man turned out to be well educated, musical, a lover of language as myself; and we shared a bunch of commonalities. Odd ones too, like being born days from one another and vacationing in the same out-of-state city the week prior to our meeting.

I can’t tell you how many times I debated telling him my boyfriend died, but I didn’t. For once, I could be with someone and be regular. He was the first new person who had come into my life, and that meant he was the only person who didn’t see me with grief. But while he was a great guy, between my commitment issues from fearing another loss and his wanting to possibly return to his home country, we cordially broke it off after the third date, wished each other luck, and parted ways forever.


Everyone’s journey is different. There isn’t a one-size-fits-all measuring stick that determines “you’ve made it,” and you can date now. I think a small part of us will never be ready because that part has been engraved with our late person’s love.

Still, if you hope to date again, you can ask yourself the questions I used to decide if it was time.

  1. Are you operating out of fear? I had huge commitment issues when I entered the dating world as a widow. Not with unfaithfulness, but with not having marriage as the end goal. Settling down? I looked for inconsistency and shallow relationships because I told myself that if he died, it’d be easier.

This often left me feeling like a person I didn’t recognize, because it was vastly different than anything I had ever been. All my actions, not wanting the man to know too much about me, not wanting to get used to seeing him, and not being serious in the relationship, were a reaction to fear. I was afraid that I’d commit, fall in love, and my person would die again before we were old.

Until you relearn how to operate out of love and not fear, you are not ready to date. This isn’t to suggest that the fear goes away completely. It does mean that fear isn’t in the driver’s seat of your love life. And, so you know, it’s perfectly okay if you want to date again but without marriage as the end goal.

  1. Can you accept that this new person isn’t going to replace the lover you lost? Before you start shouting, “No one could ever replace my person!” Hear me out. As widows and widowers, we always think and say this. We know no one can replace our person. However, having talked to many bereaved people who have experienced partner loss, we don’t always live this way.

I’ve heard conversation after conversation from men and women who said, “My late partner did XYZ and my new person does not.” It’s easy to have become accustomed to being loved a certain way by our former lover. Fortunately, and unfortunately, our new person will not be them. While it’s highly likely that we’ll attract the same type of person, we will not have the same person.

Acknowledging this is essential to a healthy relationship because we cannot force someone new to be someone of past. We also don’t want our new partner to feel they are living in a dead person’s shadow. If your actions are proving that you’re seeking a replacement rather than someone new, you may not be ready to date or need to freshen your perspective.

Dating as a widow is hard for many of the reasons one would assume it to be, but it isn’t impossible.

Dating as a widow is hard for many of the reasons one would assume it to be, but it isn’t impossible. If you want to fall in love again, I encourage you to let yourself. Loving someone new does not mean you have to stop loving your person who is gone. New love and loss can walk side by side in happiness.


What about you? Have you tried dating again, or do you have hesitation in doing so? When we share our grief stories, we normalize grief and in turn, help one another.

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