I go on A LOT of dates. I go on so many that being a serial dater has basically become a character trait of mine (or flaw, who’s to say?)

I haven’t thought too much about why I date the way I do. I’ve never questioned why I struggle to delete a dating app for more than a week or two. Or why I agree to go out with a new guy before I’ve gotten over the last one. And I’ve avoided analyzing how and why I subject my friends to 90-minute diatribes about guys I’ve only gone out with once (and will never go out with again).

Recently, I decided to dig into these things. My moment of introspection was inspired by a string of unsuccessful attempts at capturing the attention of men who were, honestly, just not interested. I needed to figure out why I couldn’t let myself have a break, and what motivated me to continue to date—even when it was no longer healthy or enjoyable.

So, I compiled a list of the reasons why people may date, even when they shouldn’t. To better identify when dating maybe isn’t in our best interest, and how dating can actually prevent us from dealing with other issues in our lives.

Here they are:

You Want Your Life to Feel Different

Now that I’m in my mid-twenties, my day-to-day life isn’t all that interesting. I do the same things and see the same people. The only change that occurs in my life is the change I enact myself. And sometimes, I get frustrated with that. Sometimes I wake up and realize I’m unhappy with how things are, and I get depressed and overwhelmed when I realize I have no clue of how to address that.

Dating makes your life feel more different than it is. Meeting someone new and indulging in those funny feelings that come with an early romance make your world seem full of possibilities. And it’s true, romance is full of possibilities—both exciting and scary.

But dating shouldn’t be used as a distraction or way of avoiding change. People can be agents of change in your life, but they shouldn’t be used to substitute your own agency. Don’t go and date different people because you’re afraid or unwilling to enact change in your own life. Instead, think about what you want and how you’re going to get it, irrespective of potential partners.

Look at your life with a critical lens and ask yourself, “what do I hate about my life, and how I can address it?” If you hate your job, start looking for other ones. If you hate your apartment, burn it down. If you don’t want to go jail for arson, brainstorm other options for the apartment problem.

Your Social Life is Lacking

Building and maintaining friendships takes work. As I’ve recently learned, you can’t enjoy the fruits of friendship if you don’t put effort into them. Your friend won’t invite you to their party if you never ask them to hang out. You will go from close friend to casual acquaintance if you don’t prioritize people.

Prioritizing people and relationships isn’t easy. Cultivating friendships and being available for people can be fucking hard, especially if you’re going through it and don’t want people to know where you’re really at.

Dating, on the other hand, is often easier. It’s social activity without the effort. You can easily book a bunch of dates to keep your calendar full, so that you feel less lonely when your former friends don’t reach out. But fleeting flings and casual dates can’t and won’t replace true friendships.

If you’re dating, you should be doing it because you’re interested in exploring romantic opportunities. You shouldn’t be doing it because it’s a quick-fix for loneliness. Fleeting relationships and flings will only make you feel emptier in the long run. And if you alienate all your friends, you won’t have anyone to bitch about your date with at brunch.

You’re Not Happy with Yourself

One of my favorite parts of first dates is the banter. Meeting new people gives me a chance to flaunt my wit and humor. It allows me to show off the sides of my personality I’m most confident in.

Date Connor is different than Everyday Connor. Date Connor is witty and he’s a great listener. He’s energetic and excited about everything.

Everyday Connor is funny, but he doesn’t always listen. His energy level dramatically fluctuates between non-existent and “omg, how much caffeine has this kid had?” He’s moody and easily distracted. He spends a lot of time laying facedown on his carpet.


Sometimes we date because we don’t want people to know the everyday version of ourselves. We want to live in the high of being that ideal person interested parties see us as. But that’s not sustainable. If you continue to date someone, they’ll see the everyday side of you at some point. They’ll get past the façade. So, you have to be sure you’re okay with them finding the person underneath.

There’s absolutely nothing wrong with putting your best foot forward. Just remember you have two feet, you binch.

You Feel You Need to Date

As I said before, I’ve dated a metric fuckton of people. It’s helped me develop a thicker skin and better coping mechanisms for conflict and rejection. I’ve stopped psychoanalyzing other people’s actions. I’ve learned to be more honest and forthcoming with my feelings. But I’ve also learned that dating simultaneously builds up and erodes your self-esteem.


The more I date, the more potential relationships that never pan out, the more I worry I’ll end up alone. It’s hard not to think something’s wrong with you when you go out with 3 guys a month and still end up single. Going on so many dates only makes it harder to quit apps because it tricks you into thinking you’ll miss out on the right guy if you delete them.

I’m a worrier, so I have an apocalyptic view of pretty much everything. Sometimes I worry that if I don’t find a partner now, I never will. I worry my physical worth is only depreciating with age. Deep down, I’m petrified that all of my friends will find their special someone and leave me alone in some hobbit hole or Harry Potter closet.

But I know that I’m still young.  I’ve handled 5 years of short-term dating with fucking gravitas. And I know I’ll end up okay, whether I have a man or not.

I’ve been afraid of missing out on the one because I’ve convinced myself I can’t be on my own. That I’m not whole or full realized as an individual. That my singleness is somehow a statement on my overall worth. As if I can’t be a great person without having someone on call to speak to just how dope I fucking am. And that’s just lies, baby.

Date because you want to share your awesome self with another person. Date because you feel ready to, not because you feel obligated to. Date because you can’t afford your utilities and Netflix subscription on your own.

Don’t let dating consume your entire life or dictate your feelings of self-worth. Don’t do it because everybody else is, or because you have shit in your personal life you’d rather not address. Dating is supplemental, not essential. Knowing when it’s right for you, and when you should take a break, can mean everything for your mental health…and wallet.