A Letter to All the Men Dating Online

Hi there,

I’m Cara. At many points over the last few years, I’ve been one of those thumbnail pictures you might click on if I catch your eye. Just like you, I’m looking for love, for connection. I’m trying to put myself out there in all the ways I know how.

I’m not sure why you’re dating online in the first place. Maybe your best friend or your sister talked you into it. Maybe it seemed like everyone you’d talked to recently had met their significant other online. Maybe you just needed to try it for yourself and see if it would work.

I’d like to take a moment here to talk a little about profile pictures. Keep in mind that this is the first glimpse a prospective date will get of you. When you’re choosing photos, make sure your pic is recent and looks like you (it might be tempting to post that long-ago photo, or the one where you look like a supermodel, but wouldn’t you rather your dream girl click on you because she thinks you look fantastic, just as you are?). I recommend finding (or taking) a photo where you’re looking at the camera. Smile as if you were sitting across from a woman you’ve become anxious to meet, eager to see if your connection is as present in person as it is online. This is not the time for shirtless selfies in your bathroom, or any picture of or with your car.

On that note, it may be that you’re an avid fisherman. I respect this. Still, you’ve got to know that a photo of you and your largest catch isn’t likely to be the most attractive photo of you. I know you want to show off your hobbies, but, instead, why not add those details to your profile and post a picture of you with as little distraction as possible. Wear something that makes you feel confident, something you’d wear on a first date, and smile. The camera might even pick up an extra sparkle of your eyes.

I’ve sat across the table at lots of coffee shops with my online dates, men not unlike you, I imagine. We met in person because of our shared interests, or because we wanted to see if we were attracted to each other in person, or because we’d exchanged a lot of witty banter. Sometimes those dates have led to multiples, even relationships or friendships, other times we’ve left the coffee shop knowing it’s probably the last time we’ll see each other.

Unlike other types of dating, online dating is unique in that you usually don’t have mutual friends or other reasons to run into each other again. It’s easy to breeze in and out of each other’s lives. Sometimes, it can be easy to forget that the person on the other end of the screen, the phone, even that coffee shop table, is just as real as you are. That person has hopes and fears, maybe she’s nervous about meeting you (or worried that you’re a serial killer). As men and women, we take a lot of risks (most of them measured and calculated) banking on the fact that one day it will pay off and we’ll meet someone great.

The men that I’ve most appreciated over the years were the ones who acknowledged that what we were doing was a little uncomfortable. Before we met, they made sure I knew that they wanted me to feel at ease. We talked about where we should go and what we should do to minimize nerves (for both of us).

This meant a lot to me, mostly because I know that dating online is a little different for guys. Your family members and friends aren’t usually sending you articles about women who are raped on first dates, or men who turn out to have secret lives. There are lots of ways you can show the women you’re interested in dating that you’re a good guy, but this is at the top of my list: express concern for her well-being. Take her safety into account. Let her know that you’re aware that she’s probably dated a few jerks, and that you’ll do whatever you can to help her feel secure so the two of you can relax and get to know each other.

If you’re talking with a woman and you don’t feel a connection, or a roadblock comes up that you consider a deal breaker, know that you don’t have to continue to talk, and you’re under no obligation to meet her. Here’s what I wish you wouldn’t do: leave her hanging. Don’t suddenly stop responding to her texts or messages. If she’s anything like me, and it isn’t obvious to her that you aren’t a good match, she might worry about you. At the very least, it’s going to hurt her feelings. It might be uncomfortable and awkward to reach out to someone and tell them you don’t see a future, but you can do it just that gently. I promise you, she’d rather have you close the loop and treat her like a person with all of the same hopes you have than wonder if you were hit by a bus. Sure, it might take you some time and deep breaths to craft a text or message like that, but isn’t that what relationships are all about? Dating can be a helpful boot camp for an eventual healthy partnership.

Most of all, I hope that you don’t become discouraged as you continue to look for love. I know that feeling of thinking that it will never happen for you, believe me. Sometimes I fight it, even now. But most of the time, I remember that the majority of us are just looking for someone who likes our quirks, our particular way of being human. Every day, I’m surrounded by people who have found someone to love them for who they are. I believe it can happen, for you and for me. Don’t give up just yet.

All my best,


Cara Strickland writes about food and drink, mental health, faith and being single from her home in the Pacific Northwest. She enjoys hot tea, good wine, and deep conversations. She will always want to play with your dog. Connect with her on Twitter @anxiouscook or at www.carastrickland.com

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