Dating When You’re Widowed

One single mother (and author) faced a completely different set of dating challenges than most of her peers in their 30s and 40s. Here, we take a look at dating again after your partner has passed on.

By Theo Pauline Nestor

ou never thought you’d go on another blind date. But then, you never expected your partner would die so soon, either. Thrown unexpectedly into the single life again, many widows and widowers have a hard time imagining they are still “dating material” or that they could ever be sitting across the restaurant table
It felt like I wasn’t honoring my husband by dating again so quickly.
getting to know someone new. And yet, the desire to connect with someone persists. “The most challenging thing that came to mind when I considered dating again,” says Penny Webb, a widowed Seattle writer and stay-at-home mom, “was wondering who in the world would want a train wreck/mother of two/grieving widow like me! I had little confidence that anyone would ever be willing to step into my mess of a life.”

When her husband died on 9/11, Abigail Carter, author of The Alchemy of Loss: A Young Widow’s Transformation (, was still in her thirties and the mother of two young children. After a few years of solitude, she realized that she was ready to date again. We talked to her about her journey into the world of online dating.

I think one of the biggest questions that comes up regarding dating after your partner dies is about timing. Did you struggle with that at all? Did you worry that you were interested in dating “too soon” or did you feel other people might be thinking that?

Yes, the timing was hard. I constantly doubted myself when I realized I was considering dating after two years. Was two years too soon? It felt like I wasn’t honoring my husband by dating again so quickly, yet I knew people who had done it much sooner. It was hard to know what “the norm” was, or what was considered appropriate by society. There were no rules. I finally realized that I had only myself to judge what felt right, so really the question was: “Am I ready?” This was also a very difficult question to answer. I had no idea. I knew I was lonely. I knew I was interested in experiencing intimacy again with another person. So I just followed my instincts.

Most single people in their thirties and forties tend to be divorced or have never been married. Do you feel that, as a widow, your dating issues are different than others within your age range? If so, how did they become apparent?

Well, I was unlike most divorced people in that I had no animosity towards my husband. I had a good marriage. I knew what that felt like, how it worked and that I wasn’t willing to settle for anything less than a good relationship, which I was only able to describe as the feeling of “being home.” There had to be some sort of recognition within the other person, similar values and shared outlook on life. Having gone through such a major trauma — losing my husband — my outlook on life changed and I realized how short life was. I knew I had to get out there and into the dating world or the time was going to slip away from me.

There were the odd occasions where I had to overcome others’ views about widowhood, which often included some form of “you’re still hung up on your husband and I could never replace him,” which I always found annoying. Especially because I was so conscious of behaving exactly in the opposite way towards the new person.

I learned that dating men who had never been married or didn’t have kids didn’t really work for me. I had two young kids whom I cared for 24/7. Someone who has no experience in that area doesn’t fully understand the implications that come along with being a lone parent.

How did you get back into dating?

I posted a profile on I had very few current pictures of myself because my role as “mom” meant that I was always the photographer, so I wound up
Most of my dates have been incredibly respectful around the issue.
cropping a photo of myself standing beside my grandmother holding my infant son. Not exactly the sexiest shot in the world, you know? I experimented over time with different photos and different descriptions of myself. I tried really honest profiles and very silly ones. I tried sweet and then sexier photos. It’s funny, though; just like in real life, you often know right away when something is going to click with a match, even online. So in the end, pictures and descriptions, though helpful, didn’t actually make that much of a difference.

When you’re dating someone new, how do you bring up the fact that you are a widow? What’s that like? Any awkward moments you’d like to share?

I have had many, many awkward first dates that usually end there. I have tried dropping the “widow bomb” in all sorts of ways. Mentioning it in emails leading up to the date is actually the easiest way of dealing with it. My date has time to process it without me having to see the stricken look on his face when I mention it over hors d’oeuvres. But there have been dates where I found myself in the rat’s hole of answering questions like, “So how did he die?” Being a widow is bad enough, but telling someone your husband died in the World Trade Center on 9/11 takes it to another level. Some people stutter through the rest of the date and make a hasty exit, never to be heard from again. I usually hear where the person was on 9/11, which can sometimes be interesting. Most of my dates have been incredibly respectful around the issue, actually.

What has been the biggest challenge for you as a widow who’s dating again?

Probably convincing myself that I was still worthy of dating at all. I had fallen into that married rut: still wearing my breast-feeding nightie to bed (my son was two at the time), buying my undies at Safeway, mom jeans, haircuts at Supercuts, etc. I regretted that. I will never allow myself to slide into complacency in whatever future relationship I find myself in.

As I began dating in earnest, I discovered a whole new world of lingerie, flattering jeans and great haircuts. I started feeling sexier and worthy of finding love, which helped me a lot. But it took time.

What advice would you give to widows and widowers heading back into the world of dating right now?

Have an open mind. Don’t fall into the mindset of thinking, “I could never date again.” Anyone can do it. Try not to hide behind your partner dying or use it as an excuse to not get yourself back out there. I know how much of a hermit you can become after being widowed. But you need to take the first step. It’s possible to meet some really nice people. Not everyone has to be a romantic interest. I went into every date thinking, “If nothing else, I will meet someone nice,” and I almost always did. I think the trick is taking the pressure off yourself.

Also, if you are dating online, you need to have a thick skin. Online dating is fickle. You may think something is going along really well with someone, and then communication just stops without warning. It happens. We all get busy and drop the ball on an email thread now and then. Online dating can be very time-consuming. If you really like someone you can try and reconnect, but if you don’t hear back, move on. Dating is the process of discovering what is important to you in a relationship. Meeting other people who are doing the same thing helps you define your own priorities.

And of course, there is always that crazy notion about having fun. Widows do know all about having fun!

Theo Pauline Nestor is the author of How to Sleep Alone in King-Size Bed: A Memoir of Starting Over and a regular contributor to Happen magazine.
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