Growing up, my mother consistently told me not to worry about men. She insisted that I needed to focus on my life and my career first and then men would come. I listened to her (although I was extremely boy crazy) and focused mostly on my future and carving a career for myself. Once I turned 25, my mom suddenly asked, “So you’re not seeing anyone special?”.
I was confused. All my life she’d warned me against men, and now I was supposed to be in a relationship? I suppose by her instruction it made sense: if I focused on my career, the men would come. But the men, in fact, did not come. In all actuality, I had to go searching for them. And I had no idea how. Until that point in my life, I’d cringed at the thought of a real date. I had no experiences to draw upon besides booty calls and FWB’s. So how did one actually manage to find a relationship? No one had ever taught me, so I had to figure it out myself.
I stumbled blindly through dating, awkwardly navigating correct protocol and trying to reconcile what I thought dating should be versus what others told me it was. I stuck to uncomfortable comfort zones because I didn’t feel worthy of being comfortable. I ran away from straightforward men who liked me openly and much preferred the company of men who made dating into a complicated journey with no map or destination. It wasn’t actually fun, but I had gotten so used to the anxiety and general nerves that shrouded me that it began to feel normal.
Once I reconciled my self-worth, I realized that I had been doing it all wrong. Dating before had been like playing Simon: I was trying to copy all of society’s moves as best as possible in order to secure the desired Instagram relationship. And understandably, none of it had worked out. Since learning from my mistakes, dating became vastly different. Hell, it was even fun. Like who knew dating could actually be fun?
So here are my pro-tips to date like a champion and actually have fun.
1. Recognize your self-worth
The most important step in the process is to love yourself and recognize your self-worth. I learned the hard way that dating just doesn’t make any sense if you don’t value yourself or you don’t know who you are, what you offer and what you’re looking for. I recommend starting here especially if you’ve had a lot of trouble trying to find and keep a long term relationship (like me). I even wrote a handy article that details ways to find your self-worth (you’re welcome).
It’s also ok if you don’t know what you’re looking for right away. Sometimes we forget that’s what dating is actually for. It’s totally fine to make notes of the things you like and the things you can live without along the way.
2. Set boundaries
You wouldn’t start any project without some sort of a plan, right? Well that’s what setting boundaries around dating is: just a plan to make sure you’re protecting yourself and getting what you need. Boundaries constantly evolve and are different for everyone, which is why knowing yourself is crucial to setting them.
The easiest way for me to set boundaries was to figure out dating behaviors that annoyed me. I would get wildly annoyed by terrible communication or people being in my space too soon. So while dating I would reinforce that I was looking for prompt communicators and people who wouldn’t mind not coming to my apartment any time soon. I would pinpoint other behaviors along the journey that would irritate me endlessly and either express the boundary or move on. And I watched how the frustration in my dating life melted away. It became clear how easily I could take control.
3. Date multiple people
I know, I know. You have a one-track mind and simply don’t like dating multiple people. Well I have a question for you. Do you really? Or do you get way too exhausted placing all your hopes and dreams on someone and don’t have the time or energy to do that with more than one person? Do you really have a one track mind or are you just trying to not get severely disappointed by more than one person?
For a long time I thought dating one person at a time was simply how I operated. But a part of me had also been trying to convince myself that focusing on more than one person was too difficult. That it was too much. That there was nothing wrong with just finding one nice man and sticking to him, even if I wasn’t exactly head over heels. Which is seriously misguided. But it’s how we’re taught to date, especially as women. That having one person was better than none at all.
While dating multiple people, it became clear why I shouldn’t settle on just one. Even when I thought a connection was sound, someone else would pop up and show me a new level of connection I hadn’t thought was possible. It was also almost impossible to pile loads of expectations on every person I talked to. It was all I could do just to keep up, which ended up seriously benefitting me. I found that I had the capacity to date multiple people because I had no expectations from them. I was simply meeting people and that was it.
4. Don’t take anyone too seriously
This is something I wish I could have gone back and told younger me a decade ago. It took 29 and a half years, but I finally learned how to not take anyone seriously (especially men). It turns out heaping piles of expectations on someone isn’t that healthy and only leads to severe disappointment or taking things too seriously way too soon.
I took everything seriously: what men did, what they said, what they meant by what they said. I poured over text messages and asked tarot cards. At the back of my mind, I evaluated them constantly to see if they’d line up with my vision of my ideal future husband. And that would only be after the third date.
I took rejection wayyyy to heart. And I didn’t want to reject anyone because I didn’t want to lose the possibility of finding something good. I was so focused on outcomes that I never paid attention to the present moment. Once I learned to stop attaching specific outcomes to specific people, dating became a lot easier. I realized sometimes when dating, all it boils down to is, ‘does this feel good?’
If it does, great!
If it doesn’t, move on.
It’s as simple as that.
5. Show up as yourself
I’ve bent and shaped myself often to please others. Sometimes, almost subconsciously, I would take note of what the men I dated liked and I’d try to be that. So if someone I was dating mentioned that they liked watching the news and staying updated on current events, I’d start watching the news and staying updated on current events. When they said they liked women who weren’t needy, I’d stop asking them for anything. I was so busy trying to be someone that they liked, I never stopped to figure out if I actually liked them.
I was a hot mess.
Dating was like a jigsaw puzzle, and after I recognized my self-worth I stopped trying to become the piece someone wanted, and began to accept myself as the unique piece that I was. I realized all I was looking for was the piece that would compliment me. And how could I do that if I wasn’t being myself?
Yes, being yourself sounds like random, generic advice. And sometimes, it’s a lot easier said than done. But I found, while dating, it was the key piece that I had being missing for quite sometime. And it actually became a lot easier to be myself after I figured out and appreciated myself for who I was and not who I was trying to be.
6. Have fun!
All the tips above inevitably led me to be able to have fun. My thoughts towards dating became less ‘ugh, I guess I gotta meet up with this guy’ and more ‘I wonder what adventure I’ll have tonight!’. I saw each new person as less of a potential boyfriend and more as an acquaintance to spend some time with. Sometimes the dates were really great and sometimes they were just ok. But because I knew my self-worth, set boundaries, dated multiple people, didn’t take anyone seriously, and showed up as my authentic self, it was always fun.
Dating right now has been more inconvenient than ever, but I found with the above tips I was still able to have a fun (and safe) dating life. It’s taken me 29 years of mistakes and a whole pandemic to finally figure out how to properly date. And to be honest? I wouldn’t take any of it back for the world. If there’s anyone out there who can learn even one thing from what I’ve learned, then it was well worth it.