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A Single Man’s Guide to Properly Interacting with Women

man and woman sitting together
Contrary to popular belief, a lot of the perpetually single men you meet really do want to tie the knot.

A few years ago, there was a single guy in my church who lived alone, had some character flaws and was slightly awkward on dates. Not only that, he regularly sported clothing that was seven years out of style. Some people wondered if he would ever get married, and they indicated it by saying things like, “It’s gonna take somebody really special to be his wife!”

That man eventually did get married, and I was that man.

Contrary to popular belief, a lot of the perpetually single men you meet really do want to tie the knot. Many of them are weary of their situations, frustrated with themselves and confused about what’s holding them back.

When I look at the single men of the church, I find that a lot of these guys have the same problem I did at one time: They just don’t know how to interact with single women properly.

If you’re one of those men, let me say this: Your situation is not hopeless. In fact, you can probably turn things around over time if you’re willing to look in the mirror and make a few changes that may involve one of the following blind spots:

1. You’re proud of being your unrestrained, quirky self.

Every man is peculiar in his own way, and that’s part of what makes us each unique. But if you’re hoping to marry a woman who’s not quite as odd as you, it might be time to rein in some of your weirdness.

The problem with the things that make you weird is that you’re used to them, so you’re the last person to notice. Well, trust me, women do notice — and not in a good way.

Think back on your interactions with ladies. Perhaps there’s a topic you tend to raise that provokes awkward conversation every time. It might be the unsolicited discussion about your fantasy football league, your intense explanation of the five points of Calvinism, or your detailed description of your Star Wars figurine collection. If you tend to talk about this stuff without noticing the boredom or discomfort in others, your conversation skills may be an obstacle to women seeing your attractiveness.

Granted, you may end up meeting a woman who’s into your favorite, awkward topic (my now-wife actually wanted to talk about charismatic theology on the first date, believe it or not). But a better approach may be to save potentially awkward conversations for later and ask her another question instead.

2. You dress like you’re trying to scare off women.

The night my wife met me, I was wearing green cargo pants and a blue Hawaiian shirt. I thought my outfit looked kind of cool, actually.

It didn’t. I looked like a total dork.

Men, we give ourselves quite a bit of room to dress in the way we want, and we just assume the women of the world think we look good. They don’t.

Remember that three-piece suit you wore to your friend’s informal party, just for fun? Not cool. How about that white undershirt that you think makes you look muscular? Actually, those pit stains make it look like you found it in a dumpster behind a thrift store. And your favorite pair of jeans? I suppose they might look kind of cool — on your dad.

Like it or not, ladies notice the way you present yourself, which means they notice your clothes and your level of physical fitness too. If you think that’s superficial, check out the steamy book of Song of Solomon. That woman gushes about how attractive her man is (Song of Solomon 5:10-16).

Consider going to a store that markets to people your age and asking one of the female associates to help you out of your fashion rut. Or have a female friend give her honest opinion on some of your potentially unfashionable favorites. Not only will this improve your wardrobe, it could provide an opportunity to work your charm.

3. You’re either breathing down her neck or pretending she’s not there.

When it comes to introducing yourself to a woman, it’s all about balance. And men who struggle to find that balance can come off as either prowlers or wallflowers.

The prowlers are those guys who, while they may mean well, have a hungry look in their eyes and a reputation for asking out women too intensely. It’s not that asking is a bad thing — I give these guys props for boldness — it’s the vibe they give off when they do it. A woman gets the sense that if she says yes, a marriage proposal won’t be far behind. This approach reeks of desperation.

On the other hand, the wallflowers are those guys who refuse to engage. They wait for the woman to make eye contact, say hello or make a Facebook friend request. Wallflowers, I’ve got news for you: If you don’t pursue a woman, it communicates to her that you don’t find her attractive. And if she thinks you don’t find her attractive, she won’t want to be involved with you.

Insecurity is usually what’s behind our tendency to be prowlers or wallflowers. Personally, when I played the wallflower with women, I was afraid of being rejected, so I just didn’t put myself out there. And if I was playing the prowler, I was usually overcompensating for my fear that I wasn’t desirable to the woman I was asking out. In either case, I wasn’t operating out of my true identity as a son of God, which minimized the most attractive thing about me.

4. You’re sexually dysfunctional.

We all have issues and are in need of constant repentance. But sexual sin has a particularly toxic effect on your ability to interact with women.

Here’s the thing: When you’re in a steady, adulterous relationship with a harem of imaginary internet girlfriends, it’s awkward to pretend like you’re truly available to the real women around you. You’re standing there in front of this relatively attractive woman at church who’s trying to strike up a conversation, but deep inside, you carry the burden of sexual dysfunction.

If she only knew what I watched three out of seven nights last week.

Don’t worry — she probably has no idea. More likely, she assumes you’re not “that kind of guy.” However, she does detect something, and it’s shame. It’s the body language, the tone of voice and the awkward laughter of a man who’s hiding something. And when a healthy woman picks up on that, she gets uncomfortable, as well she should. She’s looking in the face of a man who “has a form of godliness, but [is] denying its power” (2 Timothy 3:2-5, NKJV).

Whether you like it or not, women will pick up on your junk, even if they can’t quite figure out what it is. For example, when I met my wife, let’s just say I wasn’t at my healthiest in this area, and I still remember her emailing me and saying, “I don’t know what’s going on in your life, but I can tell you’re struggling with something. Please know that I’m praying for you.” Thank goodness she was, but it would’ve been better if she didn’t have to.

5. You’re a lone wolf.

This may sound extreme, but if it weren’t for the friends who helped guide me through my single years, I’m pretty sure I wouldn’t be married today.

My friends were the ones who said, “You said what?” after I reported the weird things I revealed on first dates. They questioned my wardrobe choices (with little success, unfortunately), and cheered me on when I showed a healthy initiative with women. They stood with me in my fight to resist sexual temptation, and they listened as I talked through years of emotional baggage that contributed to my awkwardness with the ladies.

Men, you’ve got to build honest friendships like that if you’re going to figure out how to properly engage with women. As Proverbs 18:1 (NKJV) says, “A man who isolates himself seeks his own desire; he rages against all wise judgment.” Don’t try to figure this thing out alone. You would’ve already done that years ago if you were capable of it. Besides, strong friendships are going to be vital to keep your marriage healthy one day, so you might as well get them up and running now.

I realize that God is sovereign and can bring along the right woman who is willing to suffer through your socially awkward, poorly-kempt, timid and/or sexually dysfunctional self. But is that who you want to be as you engage with the women around you? Probably not. Then as a matter of courtesy, go ahead and build alliances with some folks who will help you put your best foot forward and start becoming the man your wife will want to marry.

Copyright Joshua Rogers 2016. All rights reserved.

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About the Author

Joshua Rogers

Joshua Rogers is the author of the book Confessions of a Happily Married Man. In addition to writing for Boundless, he has also written for,, Washington Post, Thriving Family, and Inside Journal. His personal blog is You can follow him @MrJoshuaRogers or on his Facebook page.


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