The Only Dating Tips You’ll Ever Need

Dear E & V,

Your uncle might question my qualifications for giving dating advice, but I married your mother so I must be doing something right.

Dating is hard for anyone, and even harder if you’re an introvert. It took me about 10 years after my first serious girlfriend to meet your mother, and another two years after that to marry her. There was a lot of heartache (on both sides) and dumbass actions (mostly on my side) in those 10 years, but that struggle allowed me to figure out that your mother was the right person for me.

But enough of me being sappy, let’s get down to why I’m really writing to you: to give you unsolicited dating and relationship advice that I have learned throughout the years.

  1. It takes time and trial and error. My first “girlfriend” was in the 8th grade and it lasted about a week. I didn’t have a serious girlfriend until college, and that lasted about 7 months. I probably dated about 9 women before I met your mother.
    Don’t expect perfection on the first (or second or third or any) relationship. Know that it might fail (especially your first few ones) and be okay with that. Not every person will be right for you.
    I believe you have to have a number of relationships to figure out what you like in a relationship and what the deal breakers are.
  2. Leave them better than you found them. This is basically another way of saying don’t be an inconsiderate asshole. You will have to break up with someone at some point, do it in a way that is human (face-to-face) and leaves the door open for friendship (unless they’re the asshole). Even in long term relationships you always want to help them be the best person they want to be.
  3. Get out and try. Get used to rejection. You’re never going to get into a relationship without getting outside of your comfort zone and just asking people on dates. This is something that took me a while to understand because I was afraid of rejection. You know what’s worse than rejection? Living with regret because you never asked that person out.
  4. Be interesting. Want to decrease your chances of getting rejected? Be interesting! You will have lots of competition out there, so you need to differentiate yourself. Travel, volunteer, take up professional wrestling, whatever — just make it something you enjoy too. Lucky for you most people are content staring at their phones or playing video games all day. It won’t take much to differentiate yourself from them.
  5. Be interested. The worst dates I ever went on were ones where the other person only talked about themselves. A good date is a conversationalist — listen to them more than you talk to them. Ask them about their life and what they enjoy. Interest is flattery!
  6. Build your communication skills. This will make #5 much easier, and is much more necessary if you’re an introvert like me. Learn to make small talk, take a public speaking course (you can join Toastmasters for a very small fee), and learn how to write well (especially if you’re going to do app/online dating).
  7. SHOW that you care. As your mother will attest, this is one I am constantly trying to work on. I love her dearly, but sometimes I get so caught up in life I forget to show her how much I love her. It doesn’t need to be anything fancy — it could be a back massage, cooking their favorite meal, allowing them to take a 10 minute bath without screaming children, writing them a poem, or leaving them a sweet message on the refrigerator.
  8. But don’t go overboard too soon into the relationship. You will have relationships where you immediately fall head-over-heels in love with someone. Rarely will they also immediately fall in love with you, and that’s okay. Remember to take it slow so that you don’t scare them off and keep in mind that they may break it off at anytime for no good reason.
  9. Don’t linger on old relationships. You will have a breakup with someone or they will break up with you and it will hurt. Don’t linger on it, and don’t try to fix it after you break up — you’ll just go back to being miserable or making the other person miserable. Move on to find someone who is a better fit for you.
  10. Be yourself. You’ll be tempted to change your personality to get a date or a relationship with someone especially if you consider them “out of your league”. Unless this change in your personality makes you a better person (you start exercising and eating healthy, you improve your social skills, you get outside more, etc.) then you’re going to be miserable. Yes the short term benefits might be great, but long term you will be living a lie and you’ll be unhappy.

Out of all those points, I think the last one is the most important with one caveat:

Your partner/date will always like something you don’t. I like firefighting and your mother would probably never ever do it. She likes musicals, and I can’t stand them. That doesn’t make them a bad partner, and it doesn’t mean you shouldn’t support their interests and occasionally even participate.

I took your mom to go see a “Beauty and the Beast” musical because I knew it would make her happy. She always asks me about my firefighting calls because she knows I like talking about it.

Be willing to sacrifice some of your comfort to make someone happy, because it will pay off in the happiness it brings to your whole relationship.




Ken View All →

I am a Father, Husband, Cowboy Philosopher, Volunteer Firefighter, and Professional Dilettante. I am nothing and I am everything. But when it comes to our relationship: I only wish you wonder and happiness.

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