Stop Playing it Safe: Dating Advice for Young Men


The reason you’re lonely is that you act like a coward.

You look for ways to skirt difficulties. You avoid challenges, especially when it comes to establishing relationships with women.

I get it. You don’t want her to say no. You don’t want her to reject you, to leave you home alone wondering what’s wrong with you. You certainly don’t want her to tell all her friends what a loser you are.

Let’s be clear. All of that could happen. You could take a chance on a woman and she could shoot you down. She could kick you once you’ve fallen. She could humiliate you. In light of all that, here is the best advice you can hear: do it anyway.

One reason you should do it anyway is to see how unlikely it is that she will do any of those things. Even more importantly, you need to see that even if she does her worst, it won’t matter much. You’re tougher than you think.

Sitting around at home playing video games with your buddies, wasting your time on sports, hunkering down with the porn of your choice, all these are ways of protecting yourself. You are avoiding your duty.

Your duty is to get out there and pursue some women. You know you want to.

The problem is that you listen to your fear more than to your desire. Your focus on avoiding imagined negative outcomes prevents you from forming real positive connections. Your attempt to avoid the pain of pursuing female companionship only leads to the pain of isolation that you medicate with the vice of the moment.

You don’t seem to get how much is riding on this. People out there need you. Women get lonely too. You could help with that. It’s not that hard. A simple invitation from you could ease her burden.

There’s more than that at stake. Most families you know started because a guy got up the nerve to ask a woman for a date. Think about that. All the blessings of security and love a family can bestow depend on your putting down that Xbox controller and picking up the phone.

Even some people’s lives depend on your willingness to ask for a date. Families that begin as dates often bear to children. That’s right. There are people, quite a lot of people actually, who only exist because a particular man once asked a particular woman to go somewhere with him at a particular time.

My point is that your anxiety about pursuing women stems largely from your thinking too narrowly. You’re thinking too much about yourself. You’re thinking too little about others, too little about what you could offer women in your social circle, and too little about the future.

When you shift your focus from seeking to protect yourself to seeking to offer your best to those around you, something remarkable happens. You stop worrying so much about being rejected. Even if the worst happens and some woman insults you, humiliates you, gossips about you, you can shrug it off.

Men who look to women for validation get nervous. Men who know their motivations for seeking relationships are honorable and focused on giving can be confident, even in the face of derision, as unlikely as that is. Integrity is the best insulation against rejection. Cultivate it.

Cultivating your character requires taking risks, and risk is what you can’t get sitting alone in your room staring at a screen. Putting yourself on the line to invite a woman out, that is a chance to take a risk. If she says yes, you’ve got a chance to get to develop your relationship. If she says no, you’ve got a chance to develop your character. Either way, if you take the risk, you’re guaranteed a reward.


Thank you for reading this post. If you found it valuable, please share it on social media using one of the buttons below. You may also want to support my work by leaving a tip in the tip jar on the main page or by supporting me on Patreon.

3 responses

  1. What if I’m ugly and don’t want to burden children with a genetic endowment likely to leave them similarly malformed? Do I have a duty to reproduce then? What if modern life is too empty, meaningless, and undignified for it to be worthwhile for anyone, save a relative few? Should we still be having kids? And what are the limits of this procreative duty? How many personal sacrifices am I to endure so that others may enjoy this allegedly wonderful world? How much worse should one be willing to let the life of one’s first child get so that one can create and then support 3 or 5 or 10 additional kids?

    • Answering the questions posed here would require posts in themselves. Suffice it to say the general principle of considering the needs of others remains valid and applicable to all these situations.

Leave a Reply

Your email address will not be published. Required fields are marked *