Dear Dana: Online Dating Is Getting Me Down, How Do I Stay Motivated?

Dear Dana is a bi-weekly advice column for humans who engage in romantic relationships. Please send your dilemmas, issues, conundrums, assumptions, conflicts, anxieties, worriments, obstacles, complications, predicaments, queries, questions, and any other synonyms for “problems” to

Dear Dana,

I know you went on 71 online dates in two years, and I admire your commitment to finding love. 

I just told my recent online date, No. 5, that I was only interested in friendship and the relationship ended.  

For the most part, online dating has been pleasurable. I’m actually enjoying meeting strange men, and haven’t had a bad date yet. I’m serious—all the men I’ve dated so far were great. I haven’t landed a relationship yet only because the guys I like more seriously haven’t felt the same way about me, and the ones who like me, I haven’t wanted to pursue further. That’s it.  

But I’m starting to feel tired. I’m tired of getting my hopes up, or trying to keep my expectations low. I’m tired of feeling like I’m on an emotional roller coaster. Roller coasters can be fun, but after a while, you just want to get off. And that’s where I am right now.

I haven’t given up hope at finding someone special, I’m just having a hard time putting myself out there again and again and again. How long is it going to take?

I know I need to go on more dates, but I’m really losing steam. So my question is: How do I keep myself motivated?


Down, But Not Out


Dear Down, But Not Out:

I hate roller coasters and I hated online dating. I went on 71 online dates and I hated about 60 of them. Most of the time I was forcing myself to go. I was forcing myself to sip my beer, order calamari, pretend to be interested as a strange man told me endless anecdotes involving people I will never meet (“And then Jerry said, ‘Pushin’ is my thing!’”).

I forced myself to go on these dates and talk with these men and I forced myself not to say what I actually wanted to say, which was, “Look, if you’re not my husband I’d like to go home now.”

Once, I met a man at a place called The Bad Dog Tavern. He was tall and skinny, had dark hair, showed emotion with his face, and his anecdotes involving people I will never meet were actually interesting. Then, about an hour into our date, he asked me if knew what a Price Albert was. It’s a male genital piercing, and he had one, and he was willing to show it to me. Right there on the Bad Dog Tavern patio. I declined his offer.

At the end of every date I would go home, take off my shoes and my bra, fire up my DVR, and exhale. Online dating was like a job to me. Worse than a job, actually, because at work you’re guaranteed payment. In online dating you are guaranteed nothing.

One date in 71 was with a man who was my husband, but by then I had gone on 70 online dates so even when everything was going really well, when we were making out in a damn gazebo like it was the Sound of Music, I was skeptical. Because online dating had made me skeptical.

So how do you keep yourself motivated?

1) Logon and set up some dates right now. Because right now it is spring, you can walk outside without it hurting, and it’s finally still light at 7pm. People are going outside for the first time in months. People are ready to unfurl and meet new people. Take advantage of the spring dating phenomenon.

2) When you date, DATE. Finding someone you like online is a numbers game, and you’re only going to have success via this medium if you keep your numbers up. When I was actively online dating I would go on two or three dates a week.

3) When dating inevitably gets to be too much, take a break. Don’t give up, just pause. Stop checking your messages, maybe even temporarily deactivate your account. Use these moments to stop yourself from burning out or getting so cynical that when your future husband tells you that he’d like to see you again you smile while thinking, “Yeah, sure, we’ll see.”

4) Stop thinking of online dates as dates. Online first dates are not “dates”—they are interviews to see if you would later like to go on a date.

5) Don’t make a relationship the goal. Make having a pleasant evening with another human being the goal. You’ll probably get to drink a nice beverage on a nice patio while the warm evening breezes gently blow across your shoulders. You’ll probably get a window into another human being’s day-to-day life. You’ll probably get a book recommendation. Focus on these things, because they’re all you have.

The tension in online dating falls between what will possibly happen vs. what will probably happen. You will possibly fall deeply in love  You will probably have one encounter with this person, not feel incredibly drawn to him, and never see him again. But the possible can’t occur unless you force yourself to face, and reface, and face again, the probable.

You need to both be brutally honest with yourself (“I will probably never see this man again after this date”) and maintain a wholly illogical sense of optimism (“But we may also spend the rest of our lives together”).

The way to motivate yourself to online date is the same way that you motivate yourself to do any odious and seemingly pointless task: Tell yourself that, despite the fact that you don’t believe that anything will come of it, something will come of it. This is why we online date and apply to new jobs and reply to Mindy Kaling’s tweets. We know that the odds are against us, we know that this one probably won’t be the amazing opportunity that will change our lives, but we have to try anyway. Because the amazing opportunity will never change our lives unless we create a space where it’s possible.

I think of it as planting seeds. Most of them will never blossom. But then, one morning in May, you’ll see a green tendril curling out of the damp earth and you’ll know that your work was worth something. You’ll know that you had to do all of that so you could now be here. You’ll know that because you took risk after risk after risk and failed and failed and then failed again that you have now succeeded.

And you won’t know your love until you meet him. So go out there and meet him. As many times as it takes.

Dana Norris once went on 71 internet dates, many of which you may read about here. She is the founder of Story Club and editor-in-chief of Story Club Magazine. She has been featured in McSweeney’s, Role Reboot, The Rumpus, and Tampa Review and she teaches at StoryStudio Chicago. You may find her on Twitter at @dananorris. 

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