10 Things I Wish I Could Tell My Single Self

I’ve been married for two years now and looking back, I definitely could have been better at dating. I made a list of ten somewhat simple things I wish I could tell my single self so you don’t have to make the mistakes I did.

1. Stop overthinking.

This is advice I need to constantly give myself, so I think it’s necessary to give it to you, too. When I was single it was so easy to think “One wrong move and I’ll miss my wife!” It didn’t help that all the dating advice I got was something along the lines of “She’s just around the corner!”

Oh shoot, I gotta keep my eyes peeled then!

There’s no way to plan how or when you'll fall in love, even the controlled environment of online dating. If you’re paralyzed by your own anxiety, I encourage you to stop overthinking and just act.

2. Communicate more.

When I was single, I played my cards close to the vest. I hesitated to share my feelings with a girl I liked. This meant a lot of wasted time and more heartbreak than necessary.

Guys are often afraid to communicate because the conversations are hard. If you delay the hard conversations, you won’t feel bad now. Well, in reality, you’re delaying the inevitable and you’ll feel worse later.

There were some girls I needed to cut ties with and I waited longer than I should have. There were other girls I should have told how I felt sooner and didn’t. For example, before we started dating, my wife, Phoebe, almost moved on because she thought I didn’t like her. She didn’t, only because her roommate Holly blurted out “NO HE LIKES YOU!”

There won’t always be a Holly there. Communicate more.

3. Rejection will make you resilient.

I spent a lot of time being afraid of rejection. If I ever confessed my feelings for a girl it was a statement: “I like you.” It was rarely a question: “Will you go out with me?”

“I like you” is fine, but it’s not enough for communication. “Would you like to go on a date with me?” is better. That question gets you a clear yes or no. So why do we choose the statement over the question?

Because we think the statement will help us avoid rejection. We don’t want to give her the chance to say no because that means it's all over! Yes, that’s true. But rejection is never a bad thing. It makes you resilient.

After my girlfriend of two years broke up with me, I asked a girl out. She said no. I was surprised at how little that affected me. Since I survived the huge “no” from my ex, I was able to survive the little “no” from this girl.

Ask girls out. Hear “no” more often.

4. A relationship won’t fall into your lap.

My strategy for finding a girlfriend used to be: Befriend a girl, wait until I was sure she liked me, then ask her out. That strategy did not work.

It turns out, girls don’t throw themselves at you just because you’ve been their friend the longest. You need to ask them out.

Too many men use this strategy. They wait for a girl they like to look up and realize “It was you all along!” (cue end credits, etc.) Whatever movie you have in your head, she didn’t get the script.

You have to ask her out.

5. Hang out with your boys.

When I was single, I tried to hang out with girls. I figured more time with girls meant more chances for a girlfriend. This made my friendships with my guy friends suffer.

The friendships you develop with other guys during your single years are important. If you invest in them well, they will stay with you even if you lose touch for a while.

When you’re laser focused on dating, it’s easy to lose sight of these friendships. Give them more time. You’ll be glad you did.

6. Spend less time praying about dating.

This might be a little controversial. Single people should pray less about being single.

We tend to go to God when we really want something. For instance, like a good grade on a test (or a girlfriend.) But when our prayer is only about one thing, we will stop praying once we get that thing.

God is not your wingman. He isn’t there to give you girl advice. He is there to make you more like Him. This brings me to my next piece of advice…

7. Spend more time praying.

I would tell myself to spend more time connecting with God. When we pray well, our hearts are opened to the Holy Spirit. This makes discernment easier and it makes relationships easier.

When you spend more time in prayer and are closer to God, suddenly tough decisions become a little easier to make. Suddenly you become more virtuous. This is because God sends His Spirit to us in prayer and that Spirit makes us more like His son.

8. Update your wardrobe.

To be honest, this is something I wish I could tell my dating self.

Single men have a reputation of being slobs. They neglect their appearance and sometimes even basic hygiene. The bar is on the floor, so if you take care of yourself, you’re doing well.

But I wish I could tell my single self to take it one step further: update my closet.

I’m a pretty simple guy, so I really only ever wore variations of the same outfit: Button-up shirt and jeans. I bought multiple pairs of the same jeans and multiple colors of the same shirt. Not much variety.

If this is you, try mixing it up. Go to a thrift store and try on clothes you’ve never bought. Wear them for a while and if you don’t like it, just donate them back. A $3 experiment isn’t bad. Try to find a few different styles that work for you and alternate.

9. Don’t be afraid of “ruining the friendship.”

When I was considering asking out my wife, I hesitated. Not because I didn’t like her, I really did. I hesitated because I didn’t want to “ruin our friendship.”

This fear is noble. You recognize (rightly) that it is hard to stay friends after a relationship ends. So if you don’t date you’ll always be friends, right?

Wrong. There are two possible scenarios:

1. You date this girl and risk breaking up and losing the friendship.
2. You date a different girl and get married.

If you chose #2 over #1, you’ll have to end the friendship anyway. Your wife won’t like it if you’re constantly hanging out with a different woman. Even if she remains in your life, your friendship will need to change to be appropriate for a married man.

If you choose #2, you are going to ruin the friendship. If you choose #1 you might actually save it.

10. Go to therapy.

After starting a relationship with my now wife, a lot of wounds and hurt from the past showed up. I left some things unaddressed that colored the way I saw my own self-worth and my ability to love. Strong emotional events (like starting a new relationship) tend to exaggerate unhealthy ways of thinking, depression, anxiety, etc.

Even if you don’t think you have emotional problems or a diagnosable mental illness, you should talk to someone who can be objective about your mental health and has the wisdom to point out unhealthy ways of thinking.

If therapy makes you uncomfortable or you simply don’t want to go, instead seek out a spiritual director or a trusted wise person to talk to. Ask them if they would be willing to talk through major memories from your past and help you identify unhealthy ways of responding to positive or negative experiences.

Remember, your single years are a gift that you can use to improve yourself and tackle the things you need to BEFORE you settle into the beautiful vocation of marriage! While your single years can be trying at times, no chapter of life is ever perfect, even marriage.