Advice for Dateless Men

Suzanne Hadley Gosselin recently wrote a post for women called, “I’m 25 and I’ve Never Been on a Date.” She invited our female readers to ask themselves three key questions that may help jump-start their dating life:

  • Are you getting out?
  • Are you friendly?
  • Are you saying “yes”?

In response, Boundless reader Jonathan S. messaged our staff on Facebook and requested we supply a guys’ version of this topic. So here you go!

In this post, each of our guy bloggers give their advice to a man who’s never been on a date:

Are you afraid of rejection?

Andrew Hess says, “If I could go back and tell my 18-year-old self one thing it would be don’t let setbacks set you back for long. Being a man means taking risks and asking women out. The risk of rejection is part of life. During my time dating, I’ve shown different women interest and felt the sting of rejection. Most of us do at some point.

“But by God’s grace, I’ve always dusted myself off, wished her well, and kept moving. Too many guys let a bad experience keep them from taking another risk. They seem to say, ‘Hey, that hurt. That’s not worth it.’ But here’s a secret about relationships: God always works our pain for good — even the pain of rejection. Pain reminds us to depend on God, to make God the source of our happiness. Pain can help us become more like Christ.

“Men, if you haven’t asked a girl out in a while, why not? If you are afraid of being rejected, own that fear and take a risk. If she says no, she’s not your girl. But your girl is out there somewhere, hoping and praying for a guy like you. So get out there and find her. Don’t let the setbacks set you back.”

Are you worried it won’t work out?

Josh Loke says, “Often men avoid asking the women in their church or friendship circles on dates because they aren’t sure that it will work or even if they’re interested in the young lady. That avoidance usually stems from good intentions: not wanting to lead a girl on, not wanting to make things awkward unnecessarily, or simply wanting to be more ‘sure’ before pursuing. However, such behavior often hinders your ability to get to know someone in the ways that are necessary to make a decision to move onward in commitment. In other words, it’s harder to know if you want to be in a relationship with a girl unless you go on a date with her. Similarly, it’s harder to know if you want to marry someone unless you get into a relationship first.

“If you’re worried about leading a girl on, here’s something to remember: If you ask a girl on a date, you’re merely committing to a date. If either of you aren’t interested enough for a second date, that’s OK. Anyone you’d want to be dating will be mature enough to handle that. If you’re committing to a relationship, that’s all you’re committing to: to see if you want to get married. The answer could very well be no.”

Are you lacking confidence?

Anthony says, “I’ve got a ‘don’t’ and a ‘do’ for you fellas:

“Don’t make false agreements about yourself. It’s easy to believe lies like ‘I’ll never get a date,’ or ‘Women just don’t like me.’ Statements like these will not serve you in your goal of meeting a nice young lady. Instead, they’ll become self-fulfilling prophecies. It doesn’t matter how justified you feel in making condemning agreements about yourself or how safe you might feel holding onto defeatist beliefs. If the statement is not one you’d hear your heavenly Father make about you, don’t make it about yourself.

“Do know who you are. Confidence is one of the most attractive things to a woman. The key to being confident isn’t bravado or willful ignorance of your weaknesses. Confidence requires a mature understanding of yourself, a knowledge of your weaknesses and strengths, a release of the need to pretend to be better than you are and to self-deprecate, and a general comfortableness in your own skin. The most important kind of confidence comes from being rooted in the love of Christ and your place in Him as an adopted son of God.”

Are you stuck on a certain “type”?

Joshua Rogers says, “If you’re a 25-year-old male and you haven’t been on a date yet, it’s time to start asking women out until somebody says yes. I realize that some of you may have asked a number of women out, only to be shut down. And yes, I realize that’s humiliating and discouraging.

“But please don’t use that as an excuse to give up, because if you do, disengagement will eventually become a habit. And rather than connect with real women on real dates, you’ll probably fall into a pattern of fruitless Facebook gawking, endless dating app browsing, and friendlationships with women who wonder why you never ask them out.

“Seriously, what have you got to lose but your pride? Take the initiative to ask out a variety of women — including women you’re only moderately interested in. It’s good practice for humbling yourself and getting to know the opposite sex, and it may come in handy one day when you need the courage to ask out the woman you actually will marry.”


For more stories about how real men pursued their wives, check out “I Pursued,” published on Boundless in 2012.

About the Author