Challenging Yourself To Go On 100 Dates Can Teach You A Lot About Yourself, What You Want, And Men

The scene: You’re on a first date with a guy you met at your local cafe. After enough stolen glances and small smiles shared over the period of a couple of weeks, he got up the courage to ask you out to dinner, and you gladly accepted the invitation.

You got ready, met him outside the restaurant, and now you’re sitting across from him, doing everything you can to come off like the cool, calm, and collected girl you wish you were. But you can’t help but feel your nerves bubbling up. Did you just laugh too loudly? Is there food in your teeth? Wait, did he just ask you something?

It’s only natural to feel jitters on the first date, especially if you’re sitting across from a guy you really like, to find yourself overthinking every little thing you’re doing, to feel like a date is some sort of audition.

But have you ever thought about dating as a means of gathering information? As a way of learning something new about yourself? Or understanding what you ultimately want out of it? Or discovering something about men? Well, that’s what Jen, a single woman living in Los Angeles, decided to do – and to really make sure she learned something, she challenged herself to go on 100 dates.

We know, that sounds like a lot of dating, a lot of dinners that end up going nowhere, a lot of flirty text threads that just stop abruptly one day. But if dating is your way of collecting and understanding new information about yourself, your desires, and men, then there’s no such thing as a date being a waste of your time, right? Here’s what you can learn by going on 100 dates.

What You Can Learn About Yourself

He’s not the only person you’ll be learning about on your date. Dating can actually teach you quite a bit about you as a person, from your strengths and weaknesses, patterns of behavior, anxieties, and misbeliefs, to your uniqueness. 

You might discover a thing or two about how to be vulnerable without oversharing. As Jen shared after Date #70: “I still think that intimacy is scary – exposing that much of a heart is a truly delicate and vulnerable thing. But I feel in myself a more sincere openness than when I thought I was more open before…a notable shift in me.”

Or it’s possible that you’ll discover that people-pleasing is more of an issue for you to overcome than you’d previously thought, like Jen did after she decided to turn down a kiss: “I’m learning how to operate under the understanding that my feelings matter just as much as the other person’s, even if it causes a situation to be uncomfortable in a different way.”

Another thing you might find out about? Physical preferences you didn’t know you had, such as when it comes to a guy’s height or body type: “Deep down, I kind of knew [I had] insecurity over our size difference (not just height, size) – we did look kind of silly standing next to each other.”

You could even come to realize you have an attachment style that could be sabotaging your romances, like Jen did: “I had started to learn about attachment styles. … And I’d be lying if I said I didn’t see any similarities in how I sometimes behave and avoidant types. … At date number 53, I could not help but look at my lack of romantic success and wonder if, maybe, just maybe, the common denominator…is me.”

Seeing dating as an opportunity to not just discover something new about yourself, but to change and grow into a woman who’s wife material will help you feel less like you just keep batting zero, and more like there’s a purpose behind every first date that doesn’t lead to a second.

What You Can Learn About What You Want

Isn’t dating all about finding what you want? We say, absolutely. But when you haven’t dated all that much, or even just dated without any kind of intention, it’s not always easy to know what it is that you want.

Maybe you’ll find that you have a few dating dealbreakers. It might become clear to you that having similar values and connecting on a level that goes far deeper than physical attraction is important to you. “Even in an initial meeting, I really crave a connection over something. Ideally, something meaningful,” Jen wrote on her blog.

We all have a dating checklist, right? It’s helpful to have an idea of which boxes you’re hoping your future boyfriend will check off, but you might find yourself reevaluating whether the guy who’s good on paper is really the guy for you, as Jen shared: “I’m really looking for someone who’s not just checking certain boxes or similar to me on paper, but someone who has the same kind of heart I do and can walk with me in a shared sense of purpose.”

Or if you’ve never been one to necessarily have a “type” you always fall for (maybe you’ve dated nerdy guys, bad boys, and corporate dudes), you could realize that you do, in fact, have a type: “At the end of the day, I want a guy who provides for himself and isn't taking care of himself (and potentially me/our future family) through family money. … When I thought it over, I was surprised by how strong of a preference against that I felt.”

It takes time to know what you uniquely value in a boyfriend, what really matters to you and what’s lower down on the list. But knowing what it is you want out of a relationship will change the kind of guy you’ll be attracted to and how you approach romance.

What You Can Learn About Men

Your date with this guy can shed a lot of light on him – where his values lie, what kind of woman he’s looking for, or what he wants out of a relationship – but it can also tell you quite a bit about men in general. So even if things with this specific guy don’t pan out, you’ve still gathered useful information about men as a whole.

For example, whereas some guys will be upfront with their thoughts and easier to read, other guys might require a little more decoding. “With a shier guy, you’ve got to pay attention to the subtext,” writes Jen.

It’s hardly a secret that women enjoy being pursued and men like doing the pursuing, but there are times when it’d be helpful to a guy for a girl to show a little initiation. Jen says, “I think when there’s potential interest, but the timing gets disrupted for one reason or another, it helps for the woman … to reestablish interest.  ... I’ve also been learning a lot of how guys process things lately. And I think sometimes a little encouragement … goes a long way.”

We’re well aware of the insecurities we tend to feel as women on a first date (Is my outfit okay? Do I seem mysterious but not too mysterious? Is there lipstick on my teeth?), but what about what he’s feeling? Jen learned something interesting: “They really want to be accepted … I felt like I got to really learn about him and understand some of his backstory … I’m learning that it’s a privilege to be let in this way.”

It’s easy to get wrapped up in our own little world on dates. We’re doing our best to make a good first impression, to not become a “bad date” story for his friends. But it’s equally important to stop and think about dating from a guy’s perspective. You might just find that first dates feel a little less scary when you know you’re not the only one whose mind is going a million miles a minute.

Closing Thoughts

Seeing dating as an opportunity to discover more about yourself, your desires, and men will help take some of the pressure off, help you see every date as a valuable learning experience, and allow you to have fun – even if things don’t work out.

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