Ask a Widow: How Do I Start to Date Again?

At least once a week, I get a message that goes something like this:

I read your article on Vox about dating as a young widow and then I found your blog. I appreciated that you’ve written about sex and heartbreak, but I’m honestly not there yet. What I need to know is this: how do I even begin the process of dating again after a decade (or two or three) of marriage?

I know that this question isn’t about the logistics of dating. I mean, I’d never done an online dating profile until I became a widow, but these sorts of things are not rocket science (and if you can’t figure it out, you can always go to YouTube for a tutorial, like I did!) No, this question isn’t about how you find a person who will agree to share a drink with you. It’s about something infinitely more complicated.

What does it mean to start dating? What do I want from dating? How am I going to manage dating?

Okay, I’d like to say here that I am no relationship guru. I am also a relative newcomer to dating, and I bet when I look back on this post in a year or two, I’ll be embarrassed about the advice I gave. But whatever. I’ve never said that I’m any sort of expert in any area of widowhood or grief. All I can offer is my experience.

And it’s been an interesting experience. My very first foray into dating was an accident, courtesy of a man I met at a poolside bar on the very first trip I took away from my children after Shawn died. He woke something up in me, and I wanted more of it.

But I didn’t know how to do it. Again, it wasn’t like I was confused about how to enter my information in an online dating profile, or how to tell my friends to set me up. It’s that the whole world of dating scared me.

To start, I was scared to talk to anyone online. They are strangers mind you, and as a child of the 80s, it has been ingrained on me not to talk to strangers. But it was more than that. What do you talk about? How can you know if someone is being truthful? At what point in the conversation do you try to meet in person? I didn’t have any answers, and for many, many months, I hated opening up my dating apps. (Sometimes I still hate it, to be very honest.)

What else? Well, I was scared of those first moments on a date. I hated that feeling of nervousness I had every single time I was meeting someone new. I am a grown-ass woman! Why was I feeling like a teenager? Try as I might, I couldn’t get this feeling to go away.

On top of all of this, I was scared of rejection. I got plenty of it online, in the form of men who never returned my messages and others who dropped our conversation for no discernible reason. (To be fair, I did this too. I guess it’s just part of interacting with strangers you’ll never have to meet?) But more than that, I was scared of what might happen if I actually liked someone.

Of course, this led to my biggest fear, the one that still remains: I was scared of never finding anyone that I’d love again like Shawn.

If you’ve made it this far, you’re probably thinking: great, Marjorie. Thanks for the pep talk! Now I’m really excited to date!

Okay, I know. It’s awful that you’ve found yourself in the place where you have to date again in mid-life. It’s unfair that your partner is dead. It’s the worst.

But – assuming you do actually want to date again – there’s only one way I’ve found to face something that is terrible: you have to face it, one small step at a time.

Maybe this means going to a bar with friends and just seeing who you find attractive. You aren’t going to go home with anyone. But maybe you can see who you like, now that you’re looking again.

Or maybe this means you put up an online profile. Get your friends to help you if it seems too weird. Make them reach out to the first few potential people you think are cute, and then you can continue the conversation if it goes anywhere. (My awesome friends Becky and Michelle were great at this and have done it for me multiple times.)

Or maybe you try talking to the single guy you know at the coffee shop. You’re not going to ask him out, at least not right now. But you can talk to him! That’s actually a step, you know? If you do it, make sure to give yourself credit for being so brave. It’s not easy!

Listen, I’ve had my share of train-wreck interactions over the past year and a half. I pined over a man who never so much as looked my direction. I met up with blind dates who I wanted to run away from after just a few minutes. I went out with a man who I told after a few dates, “I really like you,” only to have him give me the “it’s better if we’re just friends” speech.

And once, I even got my heart broken.

Do I wish that I’d never started dating?

No, I don’t. I wish that things were easier. I wish that the next love of my life just fell in my lap and we had gotten married a year or two after I became a widow. It happens for other people, why not me? When I was first widowed, I assumed that once I decided that I wanted to start dating, I would easily find a boyfriend and that eventually, I’d find a new husband. But it is not easy, at least not for me.

And yet. What I keep telling myself is that I have to try. I’m not saying everyone has to try. My dad, for example, is perfectly happy being a bachelor for the rest of his life. If this is you, that’s great! But I know that I want more. At first, I thought that I just wanted someone to text when I was bored and warm my bed on occasion. But recently, I’ve realized that I do eventually want something that’s more long-term. And yes, I know it still might not happen for me, even though I want it.

But the thing is, it definitely won’t happen for me unless I try a little bit. So even though I’ve been through a million uncomfortable situations over the past two years, I know I have to put myself out there with dating. I have to answer the online dating profile questions, even though I really should be doing laundry. I have to talk to strangers at a bar, even though they might turn away from me after a few minutes. I have to go out with men who are terrible matches for me and I have to do it over and over again because there’s a chance that one of them will actually be a fit.

Yes, I could be content with my life as it is. I have my kids. I have my dad, my sister and my extended family. I have my rad friends and a teaching job I love. Really, dating takes time away from all of the things that bring me joy.

But I know what it’s like to be in love. And I want it again, someday.

So, dear readers, I’m going to put down my pen right now and pick up my phone and try and connect with someone who may someday want to have a drink with me. Who may someday want to know my story. Who may someday want something more with me than just funny banter back and forth on a dating website.

Maybe someday. Or maybe never. But for me, I have to at least try. Because even when we don’t know the outcome, isn’t there a beauty in trying?

**This column is merely my point of view and is for informational purposes only. I am not a therapist or medical professional, and thus my thoughts should not be a substitute for advice from these professionals. Please get immediate help if you feel like harming yourself. The National Suicide Prevention Hotline is 1-800-273-8255.