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How to Win a Woman’s Heart

guy giving girl a piggy back and looking lovingly at each other. Winning a woman's heart
There was a time during my unmarried years when I was trying so hard to get dating right that I just ended up getting it weird.

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There was a time during my unmarried years when I griped that the only women who noticed me were “old ladies, female relatives and little girls.” I wondered what was wrong with all the eligible bachelorettes who were overlooking me. I should have asked myself what was wrong with me. I might have realized that I was trying so hard to get dating right that I just ended up getting it weird.

I think back to the many first dates where I discussed my thoughts on marriage before we had even finished our meals — weird. Then there was the excessive verbal processing of every little step in the relationship — so weird. And there were the countless dates that I managed to ruin by rambling on like I was talking to my therapist. It was embarrassingly weird, and it was all done to create an artificial sense of closeness and thereby force the outcome of marriage. It did not work.

On the other hand, some of the guys I knew had the opposite problem. Where I was trying to get engaged by the end of the third date, they could never seem to make it to the first one. Either they were apathetic to engaging with women one-on-one, or they actually believed that ambiguous social interactions were enough to keep things moving — well, it kept them moving alright: toward frustration and resentment on the part of the women who couldn’t figure out where they stood with these guys.

In retrospect, I think we all could’ve used a good verbal shin-kicking to yank us out of our alternate realities. There’s no guarantee it would have actually worked (heaven knows some people certainly tried), but if I could go back in time and be the one to make the speech, here’s what I would have said.

Deal With Yourself

Before you’re ever going to win a woman’s heart, you’ve got to deal with your own. I’m not saying that you’ve got to be fully mature to pursue a woman, or no man would ever get married. What I’m saying is, if you’ve got a drinking problem, major credit card debt, serious daddy/mommy issues, a porn addiction — if you’ve dropped out of college multiple times and you can’t keep a job, please don’t invite a woman into that mess.

Get yourself into counseling, and while you’re at it, do whatever it takes to be friends with an older, stable, married guy. Be completely transparent with these mentors and with God, and ask for help in moving toward stability. Why? Because part of what makes you so weird with women is the fact that you’ve got baggage that you’re always subconsciously trying to hide. They sense it — even if they can’t put their finger on it — and it leaves them feeling slightly uneasy.

Talking and praying through your issues with these mentors will help you change and be more confident as you introduce the real you to women. A healthy woman will pick up on the fact that you feel comfortable with yourself, and it will go a long way toward helping her feel the same way. But once you’ve done the work of making yourself more emotionally attractive, don’t start aimlessly pursuing women just because they’ll say “yes” when you ask them out.

Decide Whether You’re Interested

Every woman likes a man who is interesting, but a healthy woman will only be drawn to a man who is also interested. If you’re just showing up in a woman’s life to take her for a friendly test drive, she will sense it, and she won’t feel completely safe. So figure out if you’re drawn to her before you start pursuing. It will go a long way toward helping her trust you.

I’m not saying you can’t make a move until you’ve figured out you want to marry her. I’m just saying you need to evaluate what you know about her and decide whether there’s something about her that intrigues you. If there isn’t, no need to waste her time. But if there is, don’t just sit on your hands and hope she figures it out.

Let Her Know You’re Interested

A few weeks into dating my wife, we were talking on the phone when she mentioned that she had enjoyed “hanging out” with me. I wasn’t sure what she meant by that, but I was afraid that she might have misunderstood my intentions — I mean, when I’m “hanging out” with friends, I don’t pay for their meal, wear my Friday night best, or gently touch their back while crossing the street.

So I said, “If you don’t mind me asking, what do you think this relationship is?”

“I guess I would call it a really special friendship,” she said.

“Whoa,” I replied. “Then I need to clear things up. I’m not sure where this relationship is ultimately going, but when I meet a woman who is as beautiful, intelligent and spiritually mature as you, I don’t spend time with her so that I can make a new ‘friend.’ I’ve got plenty of those. I’m spending time with you because I’m attracted to you. I just want to make sure you understand that.”

“Oh,” she said, seeming taken aback by my forwardness.

I knew it wasn’t a perfect execution, but it was a vast improvement from the days when I would have freaked her out with some over-the-top, premature diatribe about pursuing marriage. And my approach was a lot better than some of my friends, who were spending all kinds of time with women without ever making their intentions clear.

As it turns out, even though my wife was, in fact, taken aback by my bluntness, she also liked it very much. She says it brought clarity, made her feel honored, and quieted some of her nagging insecurities about whether I was actually into her.

So what I’m saying is, if you’re attracted to a woman and that’s the reason you’re spending time with her, don’t assume that’s obvious to her. Say something — anything to let her know you’re not just looking for another friendship (and not over text, email or Facebook — do I really have to say that?). And when the two of you start spending more time together, and she makes it clear the feeling is mutual, don’t stop there.

Keep Reassuring Her

It’s going to take some work to win a woman over — huge investments of time, money and humility. And as you make these investments in the relationship, they will provide little sources of momentum in your pursuit of the title “boyfriend.” The problem comes when you assume that winning that title means you’ve won her heart. It does not.

No matter how confident and emotionally stable a woman may be, she will always need to be reassured of your love — not just while you’re dating, but throughout engagement and all the different phases of marriage. That’s right. Putting a ring on her finger — even a wedding band — won’t totally resolve her lingering insecurities about whether your love can be trusted. In fact, you’ll just be getting started.

The thing is, after you get married, what you do will mean so much more than what you say in your pursuit of her heart. Your words will still matter very much, but to breathe new life into phrases like “I love you” and “You’re beautiful,” you’ll have to practice the art of thankless chores, unconditional forgiveness, unconditional apologies, random acts of sweetness, and spiritual leadership, to name a few.

If all that hard work sounds overwhelming, don’t give up.

There’s a Way Forward

Maybe you’re thinking that winning a woman’s heart will require you to act like someone you’re not. Well, you’re right; it will. And here’s why: She’s not a man — she’s not you, so meeting her unique needs won’t come naturally. That’s why you’ll need some objective, outside help from the aforementioned stable married guy, a counselor, or better yet, from a few women who care about you enough to tell you the truth.

Applying their advice will often be counterintuitive and involve making rookie mistakes as you learn the dying art of romancing a woman. But if you humbly approach the process like a student, you’ll change in ways that make you more attractive to women, and eventually, you’ll develop an instinct for helping a woman feel secure in your love. Essentially, you’ll learn how to care about her needs as much as you care about your own (Ephesians 5:28-29). And even if that doesn’t instantly result in your meeting the woman of your dreams, at least when she shows up, you’ll be better equipped to be the man of hers.

Read: How to Win a Man’s Heart

Copyright 2013 Joshua Rogers. 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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