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

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.

25, Catholic & Tryna Get Dates

Well, not just ‘dates’ necessarily—maybe “25, Catholic, & Tryna Get A Good Catholic Spouse” would’ve been a better title here—but like, *clickbait*, ya know? I digress…

From a marketing perspective, it’s definitely stupid that I’m putting this article out as the first of this series. If I had any smarts at all, I’d tease this one in 3 or 4 other articles before posting it, as it’s *undoubtedly* the most appealing topic for single young adults.

(Also BIG shouts to my friends Matt and Allison for letting me borrow their pic for this article. Katherine Salvatori is a Chicago-based photographer and took SUPER beautiful photos of their wedding.)

Just the same, I like to give the people what they want—and it’s very clear based on these surveys (which a group of my young adult Catholic friends completed for me last month, in case you missed that) that young adults want opportunities within the Church to date.

But make no mistake—this isn’t a Tinderesque, Bumble-for-Catholics, “dating for the sake of dating” mentality—rather, it’s an intentional one. It’s a reflection of the desire that devout, vocation-minded young adults have for a holy, Christ-centered marriage—and it’s one the Church should emphatically embrace.

Obviously I can’t speak for men, but I do feel I can speak for women here. Secular dating is really a struggle. It’s really, really, REALLY hard to go into a dating situation knowing there’s a good chance that your opposite will outright reject you when he learns you’re waiting until marriage to have sex, or that you want to use NFP versus artificial birth control, or that you’d like to quit your job to homeschool your dozen kids one day (I’m kidding… jk I’m not). I think many of us have been there, and it’s tough. It presents a major temptation to despair, and ultimately, to settle—because who wouldn’t rather settle than face outright rejection entirely? (That’s a rhetorical question. I’d advise rejection over settling in your marriage any day.)

I know a lot of Catholic women, myself included, who didn’t actually think there was a place in existence that they might find a holy, God-fearing man. Imagine my surprise when I realized the CHURCH was the best place to go looking for those people. And holy mackerel, it’s such a shock when you finally encounter them. I’ll never forget the first time I heard a grown man mention his “chastity” (I was like “wait… your what?”). Yeah, these people exist. Amazing.

Here’s the thing: it’s great to seek dating relationships in places where you’ll encounter people with whom you have things in common. If you really enjoy rock climbing, then sure, join a rock climbing group. But if you do meet, date, and marry someone based on your common interest in rock climbing, it’s possible you’re going to have a bad time. (Of course you could meet someone who likes rock climbing and is also a devout Catholic. I’m just trying to make a point. Goodness gracious, you guys.)

In my opinion, the Catholic Church should be (and in some very lucky communities, already is) in the business of matchmaking. Absolutely, 100 percent, I believe the Church should be actively working to connect good single Catholic women with good single Catholic men. Why? It’s the future of the Church. It’s quite literally a recipe for good Catholic children that will (hopefully, God-willing) grow up to someday be a NEW set of good Catholic men and women. It’s a recipe for an increase in vocations—we need people who will raise their children to discern the priesthood or the consecrated life. And it’s a recipe for MORE holy married couples, because let’s be honest—the world could use an uptick in all of the above!

This is why this matters so much. There’s something really, really right and beautiful about people in their 20s and 30s who’d like to be married, seeking that opportunity within the walls of the Church. How can the Church expect to engage families if it’s not catching the two at the center—the husband and wife—before they’ve made that commitment and built that foundation? Answer: it simply can’t.

Practically speaking, how can the Church go about encouraging these dating relationships and creating an environment that’s conducive to Catholic match-making? Well, there’s a lot of ways. The obvious are young adult social events and straight-forward opportunities like speed dating, etc. But quite honestly, this is part of the reason it’s so important for parishes to engage young adults in general. “So how can parishes do that, Mary Kate?” I’m so glad you asked! I’ll discuss this further in future posts within this series 🙂

As far as I’m concerned, we’ve left things up to chance for far too long (Divine Providence notwithstanding). There’s a market for Church-inspired matchmaking, and we’ve got to make it happen. So for the love of all that is holy, you guys—LET THE PEOPLE DATE.