In 2014 I got serious about dating. This is what I learned.
1. I had to give up the fantasy
If I could figure out how to make money off of my ability to find something wrong with guys I would be a millionaire several times over. There was this little voice inside me that didn’t want to do the work of being vulnerable and dating someone and maybe getting my heart broken so I would invent reasons why a guy was “a weirdo” or somehow not worth getting to know. He used “u” instead of “you” while texting, he had a cat, he took selfies, whatever.
I had to look at the great guys in my life I knew well and imagine just meeting them. They’re the best guys I know and I had to admit that they would have come off as “weird” and I would have written them off! No guy seems perfect when you meet him, you have to look past the everyday awkwardness or embarrassing mannerism and see what kind of character and personality they have. This takes time.
2. I had to learn how to speak up
I’m not a gregarious person. I wish I was but I tend to be more on the reserved side, which sucks for dating because I’m never going to march up to a guy I think is cute and ask him out. But what I learned is, I don’t have to be that person but I do have to work hard to make conversation with the men around me because that is how you meet new people. I did this buy hanging out with my most outgoing friend and telling her I was trying to become the kind of person who makes friends while they were out. Since she is the kind of person who will march up to a group of guys and start a conversation it was easy to learn from her. She was the ice-breaker and I got to boost my confidence while learning that people at bars like to talk to you — and far from being a shy person’s nightmare — it’s actually really fun.
A lot of girls want to meet someone while they’re out but they spend the night looking at their phone or being too shy or forcing any guy who talks to them to lead 99% of the conversation. This is a very, very slow path to progress! Learn how to ask questions and be social, the worst that can happen is you end up with a bunch of new friends.
3. I had to do the work of flirting when I didn’t feel like it
I was in a bit of a cycle in my single life of meeting a somewhat promising guy and texting him for awhile and then getting bored with it. He’d say something that fell flat with me and I’d get busy and forget to respond and then it seemed awkward or tiresome to keep the conversation going. I learned that I was wasting a ton of time and energy doing this! Why go halfway with a bunch of guys and then move on without finding out if we click? (And you really can’t tell if you click with someone until you’re sitting in front of them, not just texting). I pledged to only give my number out to guys I was really interested in, and then to respond to every text message I got, even if it was with a “I don’t really see this going anywhere” if we did find out we didn’t like each other.
I went on a lot more dates, and they were fun. I found that when I gave a guy positive attention through flirting, I benefited from it because he felt more confident to pursue and compliment me.
4. I had to apply the standards I had for men to myself
It was great to want a rich, mature, successful guy, but I was a little bit of a mess. When I got my act together and became a more ideal match in all the areas I cared about I was more confident about what I had to offer and my dates went better. I didn’t feel like someone was rescuing me from my hot mess 20-something life, I felt like I was a catch and I acted a lot more confidently because of it.
5. I had to compromise on some things
I made a list of each and every thing I wanted in my ideal man. It was insane! If I met Ryan Gosling on the street even he wouldn’t have made it past this list. On top of the list whittling my dating pool down to about zero, I didn’t like what it said about me. I didn’t want to be a fussy, picky person, I wanted to be loving and generous.
So, I went through my list and crossed off things that were of low-importance to me and circled things that were very important to me. I ended up with a handful of things that I truly cared about and the knowledge that while things like “tall” are great, they are not deal-breakers and they mean a lot less to me than a man with a spirit of generosity, or one who likes to read.
6. I had to stop wondering what my friends would think
No one likes admitting that they put a premium on what their friends think about their lives but we all do it. Every time I went on a date I thought about what kind of cache the guy would bring me and whether my friends would be impressed or whether they would think he was funny looking or not successful enough. It’s not fun to say, but those nasty little thoughts were present.
I had to learn how to not care. My friends weren’t going to spend the rest of their lives with this guy, I was. Would I want to spend my life with any of their boyfriends? Were they perfect? Definitely not, and I don’t care. I only judge them by how they treat my friends and whether they are happy together. It should be no different for me. 
