7 Dating Lessons I Learned From 7 Years Of Being Single


Maturing can mean failing and learning, and dating is no exception.

I spent seven years being single, very single, as in striking out most of the time and hooking up very rarely. I had one “it’s complicated” type relationship but nothing official or serious.

The good thing was I didn’t waste those years. They taught me valuable lessons about myself, dating, relationships and sometimes life. They also led me to my first serious and healthy romantic relationship. I’m sure you will find at least one of them useful.

1. Consider People Of All Body Types, Appearance Isn’t Everything

Before we speak to someone, we scan their body or at least their face. Ours minds jump to all sorts of conclusions about whether we would date them.

It’s OK to have preferences, but don’t limit yourself with inflexible checklists. If looks matter to you more than anything else, try working on yourself before finding a partner.

Here are some shallow or unreasonable physical non-negotiables I’ve heard from men and women over the years:

From Women

  • Has to be way taller than me
  • Has to be in great shape
  • Has to dress a certain way

From Men

  • Has to be way shorter than me
  • Has to be skinnier than me
  • Has to have large breasts or butt

I think this approach is backwards. Physical traits should motivate people to get to know each other and consider the things that should be the non-negotiables: personality, values and chemistry.

The guy you think is great but turn down because he’s too short or the woman you flake on because she’s not skinny enough could be the people who will bring you the most happiness. Why miss out?

2. The Dating Scene Is Not the Place to Prove Yourself

Women of various body types have attracted me, but I used to spend the most time chasing after the ones my social circles thought were “hot,” which usually meant “skinny.” I didn’t even like many of them. It was an ego thing.

I wanted to prove — both to myself and others — an OK-looking guy such as myself could date or sleep with the hot girl by working hard and being charismatic. This rarely worked and was never worth it. I needed to mature and realize dating is about finding the person who will make you happier.

3. Beware The Nice Guy (And Don’t Be Him)

The word “nice” takes on a completely different meaning in the dating world. It’s the worst adjective a person you like can use to describe you because it means they think of you as a friend. But “nice” takes on a nefarious definition when you pair it with “guy.” The nice guy pretends to be altruistic but expects people to sleep with him or date him in return for his services.

I wasn’t quite this bad. I helped women with their issues and hoped they would think about dating me but wasn’t upset when they didn’t. I enjoyed helping out rather than seeing it as a quid pro quo. Nonetheless, I met guys who were aggressive and creepy about it, ones I hope women are careful of.

I could write an entire essay on how stupid the nice guy attitude is, so I’ll stick to the cliff notes:

  • Women don’t owe you anything
  • It’s objectifying to see them as prizes you can win with good deeds
    having a spine and asking a girl out is better than only doing nice things for her
  • It’s not altruism if you are expecting something in return

Therapy helped me abandon parts of that nice guy attitude, which leads me to my next point.

4. Therapy Will Help You Kill It At Dating

Therapy helped me feel better about dating and abandon beliefs that were causing me to strike out and waste time. It will have a different effect on every client but is proven to build social and relationship skills that will make dating more fun and fruitful. After making progress in therapy, I went on more dates, most of which were fun and with great women who liked me. It now helps me nurture my relationship with my girlfriend and be mindful of issues she might not bring up.

5. Don’t Play The Texting Game

One sign of maturity is not toying with people’s minds while texting. If you feel like texting back, go ahead and do it. Don’t delay to see whether the other person will make the first move. If refusing to play the game turns off the person you’re into, they are not mature enough to date you.

6. It’s OK To Be Friends With People You Met In A Dating Context

I met one of my good friends after we attempted to set up a date via OkCupid. There were tons of delays and by the time we met up, we had gone on dates with other people. Still, we clicked in a platonic way and are good friends to this day. My girlfriend is not exactly elated about this, but she accepts it and trusts me.

I think being friends with someone you dated or met in a dating context is fine so long as the romantic feelings aren’t there. If you have feelings to the point where you only want to date the person, don’t force a friendship.

7. If You’re Striking Out, It Doesn’t Mean Anything Is Wrong With You

If you’re having trouble getting dates or finding someone to be in a relationship with, it doesn’t mean you are innately undateable. There might be behaviors or beliefs you can work on — in or outside of therapy — to guide you towards the right partner.

Luck is a factor too. It took me seven years to improve my dating life, but luck ultimately brought me to my girlfriend. I think everyone deserves to get lucky (and no I don’t mean getting laid, although that is nice too).