1. Chasing the person who didn’t want to be chased.
I thought that with the right amount of perseverance, kindness and effort, I could certainly get a guy to like me back. Isn’t that how it worked with most other things? I’d spend hours figuring out what this person liked, where I could bump into them, how to make myself seem like an interesting prospect, without overdoing it of course. Then I realized that I was doing most of the chasing and the effort was not paying off. The more I initiated contact or showed my feelings, the more he pulled away. I wish I had known to just chill out a bit more. To take a leap of faith to show my interest, but then let the guy meet me half way. I probably scared off a lot of prospects that might have otherwise been more interested in me.
2. Acting as if every relationship had to lead to marriage.
This line of reasoning went into effect any time we hung out more than three times. In my 20s, so many of my friends were moving in with their significant others, getting engaged, married and even getting pregnant. Of course I wanted any new love interest to be the “One.” But being so focused on the end goal, I failed to first enjoy the relationship before us. Most relationships will not end in marriage – they’re really for practice. I’m now a firm believer that some relationships are just supposed to be crappy. These are like the dressing room section of your local retail-clothing store. Try each other on for size, get rid of the ones that cling too tight, are way too loose or just make you feel gross.
3. Playing the Waiting Game.
After a great conversation, the request for my phone number or following an excellent first date, I’d spend hours, even days just waiting for my phone to go off. Would he call? Text? Email? Was he interested? Was he trapped under something heavy? If he verbally told me that he wanted to hang out again and then I didn’t hear from him, I’d go into panic mode, wondering if he’d met someone else or realized he just wasn’t interested. I felt paralyzed. I should have been moving forward, going about my day – not worried about someone else validating my self worth.
4. Overanalyzing every single interaction.
I can’t even imagine how many brain cells were wasted wondering what a certain conversation meant. Whether a decision to go to a bar with his friends nearby my home to watch football without contacting me meant we were over or why he seemed quiet at dinner. Eventually, I learned that it never needed to be so difficult. If the relationship had staying power, I’d hear from him and it didn’t require any hard work. If he wasn’t interested, he’d rarely tell me – another lesson to understand. He’d usually just disappear into some black hole where all ex boyfriends go.
5. Worrying about everyone else’s relationships.
In my 20s, there seemed to be an epidemic of people moving in together, getting engaged and walking down the aisle. If you weren’t doing one of these things, you had reason to worry that you’d probably die alone. It could be heard at times to watch everyone around you be happily falling in love while having a difficult time getting a second date. I wish I had just stayed in my own lane and realized that it was worth waiting for the right person. That there were other things to be doing with my 20s other than getting married and I could be just as happy. That just because I didn’t have a ring on my finger, didn’t mean I wouldn’t eventually and that I should enjoy the time to figure out what I wanted in life for myself.
6. Forgiving a cheater.
Don’t do it. Just don’t even go there. If he cheats once, he’s not capable of loving you the way you deserve. There are no excuses that you can get out of your head completely.
7. Pretending that I was ok with a casual relationship.
I liked the guy. So getting the chance to hang out with him on a moment’s notice seemed acceptable at the time. Or getting a 10 PM call asking me what I was doing that evening seemed fine – who needed to be serious all of the time? But an indefinitely casual relationship was never my style, no matter how much I pretended not to care. I’ve learned to communicate what I’m interested in without holding back. If he’s into it, we could move forward. If he wasn’t, I was just delaying the inevitable.
8. Being exclusive to a guy who wasn’t exclusive to me.
This was never a good position to be in. I’d put all my eggs in one basket, thinking how happy I was after the first few dates. How could I even think about going out with someone else when we had such a natural chemistry and I was completely smitten? I’ve now learned that there are no assumptions in the early parts of a relationship. Some people need more time to figure out what they want. If you invested enough time in a relationship and he still isn’t willing to cut bait with the competition, it’s time to part ways.
9. Forgetting to value myself.
I wish I could have given my 20-something self a big pep talk. I’d tell her to walk away from the guys that made her sad. To not accept anyone who treated her less than she treated him. To go after kind hearted people instead of just good-looking people. To watch out for the guys that have other romantic prospects in their lives, but continue to keep you on the sidelines. That it’s better to be alone, then to be with the wrong person. That the right person will not make you sweat it out so hard and will be worth all the nonsense. 
