Everyone Is Terrible At Dating So I Decided To Write This Blog Post

Everyone Is Terrible At Dating So I Decided To Write This Blog Post January 28, 2018

I was recently talking to a male friend about man’s common failure to ask women out on dates.

“Men need to be intentional,” he said. He pointed out that men today hedge their bets when it comes to dealing with women they’re interested in, engaging them casually but otherwise failing to invest.

“But I sympathize with them,” he added. “Men today don’t know how to act around women.”

I had to laugh to myself. To me—a single, 25-year-old, female Catholic—I’ve always thought my expectations were pretty clear and pretty fair. Ask me out on a date. That’s it. And I suspect that most women in my situation would enthusiastically agree.

But somewhere along the way, this simple action became a complicated formula. We could argue it’s not that easy anymore, and point the finger in one of numerous places. We could blame technology. We could blame casual sex. We could blame an increasingly-feminist society that tells us the “male-asking-a-female-to-dinner” phenomenon is sexist.

I’ll be honest: these excuses are garbage. What it all comes down to is rejection.

Fear of vulnerability (and, ultimately, rejection) keeps both men and women from engaging one another at a level that implies a deeper connection. The possibility of putting oneself out there, only to be faced with the other’s disinterest, is far more daunting than the single state we’re currently in, so we hide behind these excuses. We hide behind the complicatedness of texting, Facebook messaging, and dating apps. We hide behind the potential sexual implications that come with a first date. We hide behind the fear that the other’s political views on sex and gender might lead to an awkward shut-down. Nevertheless, that’s what it is: hiding. And friends, it’s time to come out.

I’ve got some thoughts. Here we go:


1) Always ask. Always ask. Always ask. Should I say it again? Always, always, ALWAYS ask. If you harbor any semblance of interest in a woman and she’s not spoken for, ask her on a freaking date. Here’s the thing: women know when you’re interested. They can tell when you’re giving them more attention than you’re giving everyone else in the room, or when you’re going out of your way to say hello, and it probably got back to her within minutes that time you asked her friends if she was single. Trust me, she knows. She. Knows. Chalk it up to feminine intuition and thank the good Lord for it next time you’re on your knees. Then get up and go ask her on a stinkin’ date.

But what if she says no? What if she’s not interested? Brace yourselves for thought #2, boys.

2) Rejection is a good thing. *Men reading this everywhere flip the table and swear off women for life* You guys, hear me out. Yeah, rejection sucks. It’s maybe the suckiest experience in the history of sucky experiences. Trust me, I’ve been there, as have many who’ve come before us and many who’ll come after. But that’s sort of the point: everyone experiences rejection in some capacity, be it dating or elsewhere in life. If you haven’t, I’d argue you’re not trying hard enough.

Here’s my math on this: God gave us life. He gave us free will. He gave us the birds and the bees and said “go forth and multiply” and set us loose on the earth. But did you hear that? That call to action? “Go forth.” Go FORTH. Pursue that which the Lord’s placed on your heart and proceed with confidence that He directs your path! Because here’s the important piece: a “no” from a person is a “yes” from the Lord. It’s His yes! It’s His “yes” to something else—a plan undeniably better than the ones we make for ourselves. So in those moments that rejection hurts, dig deep. Take it to church. Hear the Lord’s abounding “yes” in one, very small “no.”

And be not afraid, guys. The Lord knows what He is about. He will not abandon you, He will not forsake you. The beauty of the human person is we’re incredibly resilient. It. Will. Be. Okay.


Rest assured I pull no punches when it comes to you, because you’re of my own makeup, and I see what you’re about. You want a relationship, but you’re naturally defensive—as you should be! You’ve got an incredible treasure to defend, and I sympathize with you.

But ladies, be gentle. Our men are not so tough as their external appearances might suggest, and their hearts are affected by us. Here are my thoughts:

1) SAY YES! What the heck are you saying no to first dates for?! Girlfriend, you are very single. You are very sick of being single. You are very much spending Friday nights cuddling your pet and complaining that men never ask you out. So why—WHY—are you saying “no” when good men work up the nerve to actually do it? Say yes! Open yourself up! Stop being so stubborn!

Here’s the thing: men have quit asking us out because we’ve quit saying yes. SO OFTEN, women make snap judgements of men and turn up their noses, because our standards are remarkably high and, in my opinion, vastly unfair. Give him a chance. And don’t give me this “but what about our friendship” garbage. Girl, what use do you have for another friend? While I’m sure this kind male “friend” of yours enjoys listening to you ramble on about The Bachelor and your theories about Jack’s impending death in This Is Us, he actually doesn’t. He just wants to take you out. So please, for the love of all that is good, let the poor guy date you.

(Speaking of The Bachelor! It’s like Carly and Evan, you guys. Everyone knows Evan was the sweetest guy in Paradise that season, and Carly vehemently refused to give him the time of day. Then they had to do that weird kissing date, and she got past it, and now they’re the most down-to-earth couple in the history of the franchise. Thank you. I rest my case.)

On to my second point.

2) Put yourself out there, girls. I know it’s tough, and it feels unnatural, and you feel exposed. I know it’s not necessarily the way you saw it in your head. But sometimes, boys just need a little push. And your availability could be that nudge to send them straight over the edge.

What do I mean?

Don’t. Do not. Do NOT. Show up to a social event and stand in the corner talking to your seven girlfriends, leaving the circle only to travel to the bathroom in packs of three. Just, please don’t. Who are you kidding? You’re here to meet men. You’re not going to do it while standing over in that corner, lamenting about the fact that no one will approach you. Go talk to other people.

Don’t leave everything up to the guys. They have to lead, but we have to be willing to follow. Open yourselves up! Let yourselves be seen! And as I told the boys: be. not. afraid.

We have to be vulnerable to love, y’all.

C.S. Lewis hits the nail on the head:

“To love at all is to be vulnerable. Love anything and your heart will be wrung and possibly broken. If you want to make sure of keeping it intact you must give it to no one, not even an animal. Wrap it carefully round with hobbies and little luxuries; avoid all entanglements. Lock it up safe in the casket or coffin of your selfishness. But in that casket, safe, dark, motionless, airless, it will change. It will not be broken; it will become unbreakable, impenetrable, irredeemable. To love is to be vulnerable.”

It’s hurtful and it sucks, but it’s a byproduct of the human condition. So what can we do? We can do this: accept it as our cross in the single life, and carry it gracefully. Use it as an opportunity to pray for those who’ve rejected us. Offer it up for your future spouse. Life is long, my friends. But a long life spent with a holy, God-fearing person whom you love is well worth the rejections you might endure along the way.

"Great post! Online dating in general sometimes unfairly gets a bad wrap, but most people ..."

Everyone Is Terrible At Dating So ..."
"I am pro choice and I believe in God with goodness. Asking females out on ..."

Everyone Is Terrible At Dating So ..."
""Kids hang out in groups, and pair up as the urge strikes, or not, before ..."

Everyone Is Terrible At Dating So ..."
"I suggest that there is a larger, cultural influence that is making things more challenging- ..."

Everyone Is Terrible At Dating So ..."

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  • I know a fair number of men are afraid of being *that* guy. You know, the one who won’t take “no” for an answer and ignores clear signals, making women ever more wary of interacting with men in social situations.

    I’d add that if a woman is interested in a particular person, she should be direct in signaling availability to that person. Too often I have responded to women who seemed to be putting out availability signals only to discover they were trying to signal the man next to me, or the fellow behind me, or a guy clear across the room who wasn’t paying attention, or even other women. I backed off quickly, of course, and some of them eventually got the attention they actually wanted.

  • Elijah fan

    Divorce is the biggie unmentioned by you but a male in the usa with no fault divorce in many states can lose not just love if he is rejected in time…but he can lose house and children to the woman. And therefore he can be robbed thoroughly by risking love in the usa far worse and far more likely than being robbed in the mall parking lot by a thug. Thus years of indirection and living together for some. Ergo your last sentence is the most important….only risk with those who fear God…not just love Him…fear Him as to vow breaking.

  • MarylandBill

    With respect, this article is not about marriage, it is about taking the first baby step in a relationship. Even if you are unwilling to commit to marriage, you are not going to live with someone before you ask them out. This article is not for those people anyway. This is for the people who want to date, want to explore the possibility of marriage, but haven’t because they are unwilling to take a risk.

  • longford bill

    A good way to minimize risk is to ask the girl if she would LIKE you to call instead of just “can I call you sometime ” If she says yes well in all likelihood she might enjoy your company That is until you tell her you think Trump is great Then you will really know if she is a winner or not.
    Well written, nice work

  • Larry Bud

    This was a known problem long before texting and dating apps came along. Here’s an analysis from 25 years ago: https://www.catholicculture.org/culture/library/view.cfm?recnum=134

  • PaulB

    I suggest that there is a larger, cultural influence that is making things more challenging- we have multiple practices that make our views on dating dated- I see it with my own teenage son and his friends. Kids hang out in groups, and pair up as the urge strikes, or not, before moving on. It’s all so empty and casual, but it’s familiar, expected and comfortable for them. I’ve actually found that my kid is pursued more for not taking part in this with his friends, which is interesting too. What this implies in the long term as far as forming meaningful romantic relationships remains murky to me. Perhaps it will work out that compatible young people will find each other.
    At the other end of the spectrum, bombed from a very young age with meetooism, young men who aren’t inclined towards sexual assault are rightfully uncomfortable with the possibility of being accused of aberrant behavior. Boys are disempowered in that respect, creating a mixed message that gets normative behavior lumped in and labeled as part of ‘toxic masculinity.’ I’d note that this does have an unintentional effect of discouraging younger men from making themselves vulnerable enough to have a romantic relationship. Dating safely then becomes something of a Sadie Hawkins dance.
    For a high-quality man, then, there’s a question of risk management when it comes to dating. And isn’t that insane? Even so, all this caution and the horror stories out there put men in conflict with the biological imperative and the suite of hormones that urge us to go forth and multiply.

    I don’t think there’s a shortage of good men who are looking for quality relationships. Of those men, the ease and safety of casual relationships siphon off some. Inability to deal with the challenges of pursuing a new relationship also has a role, as the author suggests. I’d submit that the outbreak of single motherhood and lack of masculine role models, coupled with a reduction in the quality of competitive platonic relationships with other men also play a part. Men thrive and are made to thrive by competition. Eliminating the ways men can compete also eliminates a path towards healthy self-image, which helps inspire confidence.

  • TinnyWhistler

    “Kids hang out in groups, and pair up as the urge strikes, or not, before moving on.”
    I’m in my mid 20s. This sounds exactly how my grandfather describes his dating experiences. He loves talking about how his mother’s advice was “Never date the same girl twice” since going on dates was about getting to know people not about knowing instantly if she was “the one”

    Perhaps the insistence that dating be made serious has contributed to some of the issues.

  • brad

    I am pro choice and I believe in God with goodness. Asking females out on a date is not a difficult thing to do it’s some men know and understand the 3 beliefs girls have.
    Many females are pro choice with faith in God and some girls are atheist and choice.

    Religious men and women are the least intelligent they still take the bible and Koran as full truth and reject most people as overwhelming bad or not good so they hate secular culture for being money and result based.

    Asking females out on a date who are stuck up on religious beliefs it’s hard. Religious men are cry babies

    The leaves atheist men and pro choice believers in God men left . Its pro choice men want pro girls

  • Tita Shawie

    Great post! Online dating in general sometimes unfairly gets a bad wrap, but most people don’t realize that over 40% of new relationships world-wide are started ONLINE! There are a lot of good paid sites, and a few great free ones if you know where to look. For those who are more interested in Asian singles, the best truly free site we’ve found is All Free Asian Dating There are also some good paid sites like Match or eHarmony if you are willing to pay monthly fees.