Dear Me

It’s so easy to put off dating until later. It’s easier to assume you’ll get better at relationships as you get older and everything will magically work itself out. But in ten years, you might be kicking yourself for not trying harder now. The following exercises are designed to help you find motivation for dating now and focusing on improving your relationship skills now, rather than continuing to put it off.

I found exercises similar to these in a book about habit change and adapted them slightly to fit this blog. My first instinct was to skip the exercises because they seemed like a waste of time (plus, I tend to avoid anything that involves getting in touch with my feelings), but I found them to be surprisingly insightful.

I recommend writing or typing the letters, rather than just thinking about what you’d say.

Letter One:  

If you could go back 10 years into the past, what do you wish you had known about dating and relationships? Write a letter to your younger self, telling yourself exactly what you wish you had known then.

My letter

Dear 17-year-old me,

Right now, you’re very shy and you’re convinced that guys just don’t like you. You’ve never really had any male friends. You think you’ll marry the first guy that’s willing to have you, because otherwise you’ll always be alone. It will take you almost 10 years to figure out that you’re not inherently unlikeable, but when you’re not comfortable being yourself, it’s impossible to get to know you. It’s not that guys don’t like you, they don’t know you well enough to figure out whether or not they like you.

Eventually, you’ll learn to be friends with guys, by just treating them like people. You’ll slowly become more comfortable with yourself, helping you to be more comfortable around other people. Toastmasters will help a lot with that. So will travelling. In a few years’ time, you’ll reject, and be rejected by, several guys. It’ll be a little rough, but completely worth it, because you’ll learn about yourself in the process. 10 years from now, you’ll still be working on liking yourself, but you’ll make lots of progress.

Things will get better. Just be patient and take tiny steps in the right direction.


27-year-old me

Letter Two:

Now, imagine yourself 10 years in the future. If you continue living your life just like you are now, what will your life be like? What advice would your 10-year-older self give your present self?

My letter

Dear 27-year-old me,

I’m 37 and still single, which shouldn’t come as a surprise. I’ve had a couple of brief relationships that barely lasted a couple months. I’ve enjoyed the past 10 years and spent time doing a lot of things that would have been harder if I wasn’t single, like travelling, but I’m at a point where I really want to be in a stable relationship.

I’ve been waiting around for ages for the right guy to come along and ask me out, but it just isn’t happening. Even after all this time, I’m still fairly shy around guys and hate the idea of asking someone out. I still really want to have children, but the reality is I’m running out of time. All of my friends have coupled up and those annoying comments about “why are you still single?” increase 10 fold and are so much more annoying now.

Here are a few things I wish someone had told me to do when I was younger:

  • Stop waiting around for guys to ask you out. Ask out a few on your own. It’ll get easier.
  • Give some online dating sites a genuine try.
  • Spend a little more time with your friends and a little bit less time on your own. You’ll be happier with a few good friends in your life.

You have plenty of time, but the sooner you get used to dating, the better.


37-Year-old me

Did you find these exercises to be helpful at all? Feel free to share your letters in the comments.

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