20 Things I Learned from 20 Years of Dating

A startling revelation occurred to me the other day – Del Taco has been selling a version of California Burritos for over two weeks now and I STILL haven't gone to sample it!!! And my other revelation was I've now been dating for over 20 years!!! TWENTY! While others have settled down, had kids, and moved on to adulthood with grace and class, I've devolved into a slightly less refined version of my 14-year-old self. For years now, people (both male and female) have turned to me for dating and relationship advice. Why? I have no idea.

Common questions include, "There's a discharge from my penis when I'm urinating, what STD do I have?" Or, "How can I tell if the person I'm dating is an awful person like you?" Or, "How can I sabotage the brakes in my lover's car?" Or, my favorite, "Can you shut up and jump off a bridge? Stat?"

My readers love me.

You can probably ask me about any aspect of dating and I will have experienced it. If I took a class on dating, I'd get a B just for showing up, right? Probably more like an A-.

Alas, here are the things I've learned about approaching, dating, sustaining, and being better at relationships. Some of these I've always preached, but others I had to learn the hard way.

1. Learn to break up with a girl. As an extremely empathetic person, I still struggle with this one. I wish I possessed the ability to look a girl in the eye and say, "I don't think this is working out." I did that once in the 8th grade and it was the most awful feeling in the world, but it was the right thing to do. Too many people string someone along until they find someone better. Cut your losses and save your time for someone you're meant to be with.

2. Have a short-term memory. Most guys are crippled by the fear of rejection when going up to a girl. EVERYONE gets rejected. If you can conquer that fear, quickly forget and move right on, you are now better than 95% of the guys out there.

3. Don't talk a big game. After the fear of rejection, the other reason guys are afraid to approach a girl is the fear of being rejected in front of their friends. Find friends you can be real around – ones that aren't impressed with gloating.

4. Have girl FRIENDS. Sometimes there can be no better wingman than a wingwoman. Not to mention, some of my favorite, most rewarding friendships have been with girls. You don't have to worry about macho, testosterone-filled guys who frown upon the expression of vulnerability. We all need to be honest with ourselves sometimes.

5. Be a gentleman. It's never too late to adopt habits of opening doors, pulling out seats, helping a lady put on her jacket, and offering your own jacket when it's cold – these acts go a long way. If you're not considerate in these realms, I'd imagine you're probably horrible and one-sided in the sack as well.

6. Dance. If you've spent ANY time with me at an establishment with music, you know that I like to dance the night away. It wasn't always so. In high school, I was definitely mortified at the thought of my loose limbs flailing around. Dancing, no matter how bad, is always better than NOT dancing. It's the best way to break contact with a girl.

7. Wait to buy a drink. Don't ever use buying a drink for a girl as the prerequisite for talking to to her, especially if the girl is the one who asks you to buy the drink. I only buy a girl a drink if we're having great conversation and/or I'm getting a good vibe. You'll save yourself a lot of money and the needed brain functionality to remember the conversation you have with someone who actually matters.

8. Be kind to service industry professionals. They put on a show everyday by smiling and cleaning up after the worst of you. The least you can do is smile back, help clean up your own stuff, and tip. Your date will notice more often than not.

9. Read current events. If you want to have a conversation with anyone, you'll need to expand what you know of the world. What better way than to read the news everyday, so that you can talk about a broad range of topics. Who knows? Reading may even be able to help you figure out the daunted "your/you're" and "they're/their/there" – it's not that hard, people.

10. Live in your skin. Katy Perry (yes, I listen to Katy Perry) sang, "I fell for everything, because I stood for nothing." Too many people only know themselves as part of a relationship – never taking the time to find their own interests or be comfortable with who they are. The more you know about yourself, the more engaging you can be with others.

11. Communicate. I don't think any girl I've dated can say that I wasn't a good communicator. Don't let things go unresolved and allow them to fester. Handle your business by communicating and enjoy a much more productive relationship with fewer issues and probably a more open, fulfilling sex life.

12. Listen. Be interested in people. Ask questions. Really get to know someone.

13. Don't play games. Real men don't play with people's emotions. Sure, there's still some subtlety that goes into when to text a girl and what all you can say at the beginning of a relationship, but if you know you don't like a girl as much as she likes you? Cut her loose. Even if the sex is amazing. It's not right to her. (This goes the same way for you ladies.)

14. Date someone who likes their job. There's nothing more draining than someone who dreads going to work and then comes back with a heart and mind full of annoyance and disdain. Rather than enjoying each other, you're spending large amounts of your time listening to someone vent and then trying to cheer them up.

15. Overvalue intelligence. I've been very guilty in emphasizing looks, while devaluing important things that will help a relationship last when the looks have faded. In all my 20 years, I can now tell you – definitively – that intelligence is sexy. You almost certainly cannot be funny (to me) without being intelligent.

16. Don't take yourself too seriously. I am often the butt of jokes, which does not bother me whatsoever. I encourage it. If I have to be self-deprecating to get everyone to loosen up, then I will happily do that.

17. Enjoy the moment. While you've inevitably heard the phrase, "the joy is in the journey," I can't help but again emphasize that there is joy in every moment. It's not always about being AT the concert or enjoying the finished meal – sometimes the gems can be found while stuck in traffic or making a mess in the kitchen. Enjoy it all.

18. Don't be jealous. Always believe that if someone is dumb enough to cheat on you, then they don't deserve you. You can't handcuff someone for the rest of their lives so that he/she's with you forever. Know who you are so that you don't question who you aren't.

19. Want to be a better person. We can always improve upon who we are. Whether that's mentally, physically, characteristically, or morally, we all have a lot of room for growth. Find that person who always challenges you to be better – not through them telling or nagging you, but from them inspiring you in ways to seek it for yourself.

And, finally... my favorite...

20. Be passionate. Whether it's a moment stolen on a busy street, or a quiet walk in the park, savor your loved one when you can. Grab her, feel her, forget everything else but those lips. Linger. Sigh. But feel those lips.

I can't tell you much about marriage or raising a child (I look forward to it one day), but I can tell you to love your life. Love the fact that you can love. We spend a lot of time figuring out who we are as people – it's an ongoing process – but the new people we allow into our lives can be transcendent. While you may not spend forever with them, there's so much growth and love to be had.

Love to love.

Kevin L.

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