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  • Writer's pictureMonica Montanari

My Foolproof Guide to the Dating Game

Asking for dating advice doesn't make you pathetic- let's start with that. These days, dating is easily the most complicated part of life for many. Technology has changed the game (yes, it's totally a game) of dating, in ways that can be super confusing if you were raised on good-old-fashioned courtship. It's a tough, tough world- but this post aims to untangle the mess a bit and show you, regardless of any factors, how to get the one you want.


1. Don't.

No, seriously. That's the first step. If you really want to find a long-term person, stop looking. There are two great quotes that come to mind. One is: "become the person that the person you want to marry would want to marry". The other is: "some of us are becoming the man we wanted to marry". Regardless of gender, let's think about that.

Quote #1: All your life, you've probably been busy thinking about the attributes that you want to find in the person you aim to spend the rest of your life with. You're so busy putting the responsibility on someone else (it's their job to be perfect, and your job to find them) that you forget you have a much greater responsibility than you realized. Let's say you find the perfect person. They're everything you've been looking for. They're physically fit, smart, driven, financially independent, etc. The only problem is: what if you've just been sitting around waiting for Prince Charming (or Princess Charming- is that a thing?) to find you? Meanwhile you've become a slob (YES, LOVE IS PARTIALLY ABOUT LOOKS- THAT POST IS COMING I PROMISE YOU). You've lost all motivation because it took you so long to find this perfect person. You were counting on someone else to build you an empire- while you sat on your a** and watched Netflix. Dude. Why in the world would that person want to be with you? Wouldn't they rather find someone else whose ambitions and drive and goals match theirs more closely? In sitting and waiting, you've thrown yourself out of their league (in a bad way).


Quote #2: Instead of sitting around wishing you could figure out where that perfect person is hiding and dreaming about everything they'll provide you with, you get sick of being dependent, and decide to take matters into your own hands. Instead of waiting for someone to love you, you give yourself the love you've been desperately seeking elsewhere. Instead of waiting on someone to build you an empire, you earn your own way to financial freedom, and gift yourself with the things you want. Instead of hoping somebody will come along and know how to unclog a drain, you do it your damn self. Nothing is sexier than someone who has their sh*t together. And instead of waiting to find happiness in someone else, you find happiness within yourself- a sustainable kind that makes you a better person; a whole person; someone who has a lot to contribute to a relationship. You know that when you're looking for love, you'll almost certainly not find it. So you stop looking, and start being a boss. It's not easy, but it's worth it.

2. Find the right f*cking person.

Be yourself.

Let's say you accidentally stumble upon someone that's got some real potential. Or you just completely ignored my advice. If you try too hard to be the perfect match for this person, odds are, you'll end up creeping them out and abandoning everything you worked so hard for. Or, worse yet, what if they fall in love with a 'you' that isn't really 'you' at all? As the saying goes: "you aint gotta lie to kick it". If someone can't fall in love with you for who you really are, they're not the right person. Or they'll wait until you're taken and then decide to try to get you back. (Happens every time- f*ck you people). Being true to who you are is the best possible option- be weird, be funny, be awkward, be pessimistic, be real; whoever you are, just be you.

4. Get their contact info.

You'd be surprised how simple this is- but it's often so terrifying to people that they won't do it. Or they'll try to social media stalk the person afterwards. Come on. One of my favorite lines is walking up to someone and saying "you look so familiar- have we met before?". Works every time. Gets you into a conversation about where they grew up, what they do, how old they are, etc. The possibilities are endless. Just be careful not to let it die.

Worst-case scenario: stalk them on social media. Add them, then DM them or message them. But don't make it creepy. Just keep things light and casual. I.e.: "I saw you tagged in my friends photo and had to DM you. You're cute af."

"Okay so I started talking to them, but now what do I talk about? How do I continue this?"

5. Have a conversation.

Ask questions. If they give you short answers, it could be a sign, or they could just be stupid. That's pretty common so it's kind of hard to tell. I could give you lists of people who I thought hated me at first, who ended up loving me (supposedly). Don't give up too early. Piggy-back on whatever the previous statement was. So if you ask where they went to school and they literally just respond "UC Whatever", tell them an anecdote about this one time you went to that area- or your friend who went there- or the rumors you heard about that place. Whatever it takes. Try to let your personality shine through in your messages, and keep them short. Nobody wants paragraphs. Nobody.

6. Stay mentally and physically pre-occupied.

I'm not going to lie. If you know me, you know I'm 0-100 real quick. I live by this philosophy that I might not wake up tomorrow. Or you might not. So why sit around and play games? So naturally this is the advice I'm giving you that I suck at following myself. When I first fall for someone, I naturally think about them all the time. I like to think that's how other people act too when they're head-over-heels for somebody. Regardless, I literally have to give myself reasons to NOT talk to that person. I work more. I pick up some new hobby. I date someone else (horrible advice don't ever do that). The point is, keep yourself busy. In this case the old adage is true: often people want what they can't have. I'm not saying to play hard-to-get. But I'm saying to have your own life. To be comfortable regardless of whether that person wants to marry you or decides to ignore you for the rest of eternity (there's a special place in hell for those people). The less emotionally invested and dependent you become on that person, the more real the emotions between you will be. Give it time.

7. Get them in person.

One-on-one. Mano y mano. This is the only way you can get to know someone. I highly recommend you do it in public. It's tempting to just meet up at one of your houses and go from there. But it establishes this sense of comfort that you don't want that person getting yet. You want to send a clear message that you are interested in getting to know them on a real level. Because let's be honest: it's not that far from the living room to the bedroom.

Anyway, go somewhere in public. It gives you a good idea of who they are around other people, and how they treat the people around them. Plus, if someone recognizes them, it's a perfect way to see how they interact with old friends and/or fans. Are they grateful for those people and their support? If they hate that person, will they still treat them decently? Will they be fake? Are they naturally a flirtatious person? The possibilities are endless.

8. Take your time.

The best things in life take time. Yeah, if the person you're seeing is hot, it's tempting to just go for it. But I promise, the anticipation is half the fun. Some day when you're settled down with someone, you'll miss the feeling you got when you would get a random text from them or when they'd plan a date. You don't need to interview them immediately to get their whole life story. If they're worth it, you'll get to know them in little pieces- like a puzzle being put together. If you get more information right away, fine- but if not, give it time- and go back to my previous point about being mentally preoccupied.


I know it's hard to believe- and it only gets harder with age- but I can promise you: if you focus on being the best version of yourself while leaving your heart open to the possibilities, the right thing (aka person) will find it's way into your life.

Then again, I have a 100% fail rate so far. So...


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