How can I stay positive when dating makes me miserable?


I wanted to peel back the curtain a little bit and talk about something that I know is on a lot of readers minds. Many of you out there feel absolutely miserable about dating. The rejections, the lack of responses, the bad behavior from your dates, the whole song-and-dance of dating is making you miserable. You know what, I hear you, I understand, and sometimes I’m right there with you. Maybe not at this very moment, but I understand that dating, whether online or offline, can make you miserable. Sure, you can try to be indifferent about a rejection or two, but it’s a lot harder to be indifferent about 10 rejections, back-to-back. Okay, maybe your story is a little different and it’s more like you’ve dealt with 10 “fuckboys” back-to-back, or 10 “gold diggers” back-to-back, or whatever else you’re currently struggling with. I’ve been there before, and when I’m single that feeling comes and goes, but trust me, you can probably get over it. Here’s how I do it:

Connect or reconnect with the people who matter to you

This is as simple as calling my mother or my sister and saying “You wont believe this b.s. I have to deal with dating in NYC!” which is something I genuinely do, or it could just be commiserating with my friends. If you want to take it one step further, and this I cannot recommend enough, when you’re connecting or reconnecting with the people who matter to you DO NOT TALK ABOUT DATING. There comes a point where the cathartic effect you get from talking about the thing that bothers you is replaced by the anxiety you build up by bringing up your stressors over and over again. Just try to talk to your friends, or family, or whoever else about things other than dating if you’re finding that talking about dating makes it worse. Ask them what’s going on with them, or bring up something you’re happy about, or just talk about the weather. Sometimes you just need a distraction and a reminder of what really matters.

Reevaluate why you’re dating and how you date

So, why are you dating? Is it to test the waters, or meet the one, or to pass time? I’m not saying you need a “good” reason to date, but you should know the reason why you date. If you’re dating just to date, have no interest in a long-term, or even short-term partnership, don’t want casual sex, and don’t even really want to meet people…why are you dating? You should really think about why you’re dating, and not why you THINK you should be dating. Are you dating for yourself, or for others? Even more importantly, you need to ask yourself why you date the way you date. Let’s say you’re like a lot of people and don’t actually enjoy dating online, or using Tumblecupid or whatever you’re currently using to find dates, but you’re still doing it. Why are you still dating online? If you’re the type who is busy a lot, or has approach anxiety, you might think that online dating is the lesser of two evils. If you thought that, you’d be wrong. Dating isn’t a binary system where you choose either online or online, there are countless ways to meet people.How do you think people in the 1960s who worked weird hours and/or were antisocial met people? Bars and clubs, social events, friends of friends, matchmakers, through work, at their houses of worship, and lots of other ways. Online dating as we know it is only 21 years old (If you’re a pedant, yes a rudimentary version of online dating existed before debuted in 1995, don’t split hairs with me) so if billions of people before you could date and meet people without online dating, so can you. The Blonde of First Date Purgatory recently posted this piece on realizing that online dating just isn’t her thing and if it resonates with you, maybe online dating is for you. Don’t be afraid to date your own way.

Make changes to how you date

This one is optional of course because let’s face it, some parts of your dating life you just aren’t going to change. When I get down about dating, it’s for one of two reasons. The first is that I was excited about someone and things didn’t work out. The other reason is that I haven’t been on a good date lately and the combination and repetitiveness of bad dates, rejections, or just not meeting anyone has gotten to me. These aren’t things that I can change so I just try to move on and get over it. But luckily, you aren’t me, so if you find that you can make changes, like deleting all the dating apps from your phone, go for it. If it’s something else, like dating people with a specific profession, maybe stop doing that? Looking at you women who only date finance guys, lawyers, or men in uniform with the same results. Same goes for the guys who only want to date bottle service girls, hookah lounge hostesses, or Instagram model/laxative tea spokeswomen. (No shade to those professions, keep getting those checks y’all). If you’re dating the same people over and over, with the same results, switch it up. That goes for the professions I listed, but can apply to any profession, or any other commonalities. If all you date is teachers, or actors, or writers, or people who think the earth is flat, and they all show a pattern you dislike, stop dating them. It’s up to you to figure out what can be changed about how you date, if anything, in order to  improve the process for you.

Learn to accept the bad parts of dating

All the work you do, and all the changes you make, and all the introspection in the world will not change the fact that sometimes dating just plain sucks. Rejection sucks, thinking you’ve found a great match who inexplicably loses interest without warning sucks, and investing time and money into someone to have them just up and ghost sucks. Dating can be sublime, and it can also suck, so you’ve got to learn to accept the things that suck, that you cannot change. I’m not the religious type, like at all, but this idea can be best summed up by the serenity prayer:

God, grant me the serenity to accept the things I cannot change,

Courage to change the things I can,

And wisdom to know the difference.

Substitute “God” for whatever you believe in, even if it’s yourself if that’s your thing, but the message is the key. Accept it if you can’t change it, change it if you can, and try to recognize the difference between the two.

Take a break, or breaks

You know, sometimes it just gets to a point where you’ve made changes, learned to accept what sucks about dating, and you still just need a break. I’ve done and I’m a big fan of it in short, frequent intervals. Breaks are important because they can give you some perspective. More importantly, dating is hard work, and your hard work should be rewarded with a vacation. Maybe it’s just a mental vacation, but sometimes you just need a break, you know? Whether it’s a year, month, weeks, whatever you decide, maybe consider going on a dating hiatus to recharge yourself so that when you do date, you’re doing it from a place of genuine excitement and enjoyment, and not treating it like a chore.

The biggest thing to takeaway from all this is that you don’t need to date in any way other than the way YOU want to date. Don’t want to date online? Don’t! Want to take a break? Go for it! Do what you want, when you want it, and don’t forget to recharge by talking to the people who matter, or just take a break from dating. Date the way you want to date, and it’ll make dating a little less miserable.

Good Luck Out There.

4 thoughts on “How can I stay positive when dating makes me miserable?

  1. Hey, I count myself lucky for having found this short article. It’s full of genuinely useful advices, like taking a break and figuring out what exactly we want from dating.
    I’m in the middle of a really awkward situation where I traveled over 6,000 miles and spent a ton of money to meet this guy. He’s like ‘meh’ and I have to be in his house for the pre-planned duration of my stay in his country of residence. I want to bury my head in the soil and only leave after all sense of inadequacy wears off. It doesn’t help that I have these self esteem issues and that everything in his life is so fine (he’s got money, good looks, nice job and I have a partially disabled dog).
    Ok, enough self pity, thank you again for the article and may we all find in ourselves what we so desperately look for in others. All the best.


    • I’m glad you found this post and I’m glad you found the tips inside useful. Sorry to hear about your current situation though. I was in a similar situation once, though the travel was a lot less than 6k miles, but I know what it’s like to travel to another city/place and be stuck with someone who is just sort of “meh”. Luckily the stay will be temporary. No need to apologize for describing a situation you’re in. I wouldn’t even call it self-pity, more an acknowledgement of feeling awkward and a little bit insecure about a dating situation. It happens to us all, and if no one shared their dating stories, experiences, or concerns I’d have nothing to write about. All the best to you as well, and thanks for sharing!


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