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Episode 224: Swipe Right for Wisdom: 14 Lessons From 3.5 Years of Singlehood (Part 1)


Tomorrow is Valentine's Day and you know what that means... we recorded one of my favorite podcast episodes of the year! Truly the only thing I love talking about more than health and wellness is love and relationships. 

In year's past I've brought on the experts - one year it was a sex therapist, last year it was my parents who have a beautiful marriage after 35 years (definitely go back and take a listen if you weren't with us back then). 

But I think at this point I'm a bit of an expert in my own right. I've been single for nearly 4 years, I've gone on easily over 200 first dates (don't judge), and I have gone through many phases of growth, many realizations, and many mini-heartbreaks. 

So I thought what better way to spend this Valentine's episode than to share this real-world dating wisdom that I've accumulated?

1. Sometimes dating a lot is great, sometimes taking a break is great. The important thing is to know why you're doing what you're doing.  

You may have balked when I mentioned that I've been on over 200 dates. But here's the thing, my brother met his wife on The League (one of the many dating apps), and the way he got there was treating it like a numbers game. He would sometimes go on 2 dates in a day, 4-5 days a week, figuring eventually with enough inputs he'd get the output he wanted. And it worked! 

So for the first year I followed suit. If I averaged 3 dates per week that already put me at 156 dates that year.

And for some people that works. 

But in hindsight, that approach hurt me in 2 ways:

1. I was definitely using it to escape the anxiety about being single as I headed into my 30's. And I'm a big proponent of making sure your actions come from a place of 'running towards' instead of 'running from'.

2. When you're swiping that much, you lose the humanity of dating. Everyone becomes a check list that either matches up or falls short. And the second you see a flaw it's easy to think, "Well, that guy I'm going out with tomorrow could be better." Grass is greener syndrome is real ya'll. 

On the flip side, there were times I would stop dating out of sheer burn out and frustration. I would get angry at the universe for keeping me from my person, and grow resentful of my single life. 

This is obviously not a desirable place to be either. 

But eventually I found a middle ground, and of course it came from dropping into my body instead of looking for answers from others. Instead of listening to my brother arguing for the numbers game, or my friends saying I needed to stop trying so hard, every day I asked what felt good that day. 

Sometimes the thought of swiping sent a rush of anxiety and resistance through my body. Sometimes it made me feel giddy and excited. Which brings us to our next piece of wisdom...

2. Only swipe when you're feeling flirty. 

Imagine you're at a bar. And as you sit there you're stewing about how annoying it is to be single. You have a chip on your shoulder, you're exhausted from putting yourself out there, and despite seeing cute guys around you you can't help but assume they're all duds. 

A) Do you think you're going to attract someone great to you when you're in this energy?

B) If you do attract someone, do you think you're going to form a strong bond or do you think the interaction is going to be stunted?


So why on earth would you bring this energy into swiping? It's never going to turn out well. 

When I adopted the practice of only swiping when I was feeling fun, flirty, and optimistic, my experience on the apps improved drastically. 

3. It doesn't matter if they're perfect on paper - if you have to convince yourself you're interested, you're not. 

This one is a bit tricky to navigate, especially when you're online dating. Because there's always the possibility that first date jitters got the best of them and so you either only saw an uptight version of them or it blocked chemistry from igniting. 

But at the same time, I do think when you meet your person it should be easy to want to be with them. You should be excited to see them again. That should not be the hard part of dating. 

So my general rule was if it wasn't a hard no on the first date, I'd give them the benefit of the doubt and try again. But after that, even if they were successful, smart, funny, and kind, if I found that I was talking myself into seeing them again, I'd stop myself and end it.  

4. Put yourself in situations to meet like-minded people. 

When I got serious about meeting someone, I put my money and time where my mouth was. 

I joined a soccer league despite thinking I hated soccer (ended up having a blast, but also a big reason for joining was meeting men who were into fitness in some capacity). I showed up twice a week, went to their social events, and really made it a big part of my social life. 

I also joined Equinox. It was way more money than I wanted to spend on a gym, especially since my apartment has a gym. But I knew two major values for me were health and ambition and I figured both of those would be checked off by the members of that gym. 

Spoiler alert: I just started dating a great guy from Equinox and I'm having the time of my life! 

5. What you think is important might not be that important. Can you pick your top 3 values and let the rest go?

One day my girl friends and I were talking about dating and my friend Laura said, "We can all write out a list of 20+ things that we would want in a perfect partner. But that list can fuck us up and make us overly picky. If you had to pick 3 non-negotiables and let everything else be a 'nice-to-have' what would they be?"

This question changed the game for me in dating. I definitely was guilty of going to the  extreme with my perfect partner list and writing people off really quickly when they didn't stack up. For me this was definitely a reaction to having way too low standards for way too long, and I might have overcompensated a bit. Whoops! 

But this question brought me back to balance. I knew being health-minded was vital, it's such a huge part of my world and that was never going to change.

Being growth-minded was my second one - be it in career, personal development, within the relationship, I wanted someone who was always looking to improve. I want a relationship where we foster each other's growth and evolution. 

And finally I wanted someone adventurous. The thought of living a life where every night we order the same food, watch the same tv shows, and have the same conversations makes me crawl in my skin. I thrive when I'm collecting experiences, getting outside of my comfort zone, and experiencing all the world has to offer and I wanted someone who was down to build that kind of life with me. 

6. Don't let other people's advice overtake your own intuition.

I have a friend who is a relationship coach who I absolutely adore. And we had a lot of conversations about masculine/feminine roles and expectations in dating. In the past I was deep in my masculine in my relationships - I made more money, I did a lot of the 'leading' on dates, I planned for the future, and I took on a lot of the responsibilities of the relationship.

So in an attempt to become more feminine, I hyper-fixated on the guy needing to plan every date, to pay the bill, to text, to pursue. And if he didn't do those things I viewed it as a character flaw and created all sorts of narratives in my head about him. 

Then I started dating Gym Crush. We had the most incredible, electric dates that left me grinning for hours afterward. But our first few dates were very last minute (because we'd usually just leave the gym together and go find some food or drinks). And the man did not text between dates. 

This friend of mine (and multiple others) cautioned me that it sounded like he might not be as interested in me as I was in him, or that he at least wasn't taking me seriously as a potential partner because if he was he'd be texting and planning dates in advance. 

In the past I would have thought so too and I'd probably say the same thing to a friend in this scenario. But somewhere deep in my gut I just knew it didn't have anything to do with me, or his interest in me. 

And as I got to know him, I found I was right. 

My brother said recently, it's dangerous to think everyone thinks the same way you do. 

And for Gym Crush, texting regularly is just not how he operates. He is one of the most in-the-moment people I've met and it's honestly incredibly refreshing. It means he's present when we're together and is a great balance for an over-thinker/planner like me. And when I brought up the texting, he responded incredibly well and started making an effort to communicate more between dates right away. Ta-daaa!

Had I assumed everyone was right - that he just wasn't that into me - I would have emotionally shut down and might have even ended it. Instead I'm dating someone I'm truly excited about for the first time in ages. 

7. But definitely get other people's advice. Especially in early dating. 

In early dating I can get really in my head. I don't have a lot of practice with those first few weeks of getting to know someone. My experience has been mainly full blown relationships or first dates that didn't go anywhere. So I haven't had to navigate those uncertain waters of liking someone but not being in a relationship since my mid-twenties. And that uncertainty can lead to me acting from an anxious place instead of an authentic place. 

So it helped to talk through things with friends, to ask for their advice, to hear their wisdom and feedback. Because they didn't have any attachment to the outcome and they were a constant reminder to just be myself (even though sometimes they had to remind me what being myself looked like in that moment). 

Had I known just these 7 pieces of wisdom I would have saved myself a lot of time and a lot of bad dates (but those stories are for another episode), and this is only scratching the surface.

I have 7 more dating insights coming at you in part 2 next week (my absolute favorite one is coming up so you're not going to want to miss it). Click here to subscribe to the podcast to make sure you get notified! 



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