Asking a girl on a date is not a marriage proposal – don’t treat it like one

Those who have listened to my podcasts will have heard me use this phrase. And since I talk about it so much I figured I should probably explain myself, even though I know I’m risking the general ire of my male audience.

What I mean by this is that some men (especially in the Catholic world) treat the prospect of asking a girl out with the weight and meaning of a marriage proposal.

Think I’m exaggerating? I know two guys who spent three years working up the guts to ask a girl out, and another who spent a year finding out everything he could about a lady and speaking to anyone who knew her for intel before asking.

Not only does this attitude treat the prospect of a coffee with the gravity of a life-altering situation, it seems almost certainly doomed to fail, for a few reasons:

  1. It’s unappealing. When you’ve put your hopes and dreams behind a yes-or-no question, it’s already way too charged. Women are intuitive and they sense this. We get it’s personal and you’re putting yourself out there, but when you’re treating it far more seriously than we are, that makes for an automatic turn-off.
  2. It puts too much pressure on the woman, for the same reasons as above. You’re putting your deepest hopes and dreams on someone – that’s too much pressure for anyone! And it’s virtually impossible to fulfil.
  3. It also puts too much power in the hands of the woman; and if she’s petty or mean-spirited she might just hurt you far more than you otherwise would be, perhaps through careless speech or because she wants to feel better about herself by putting you down. In short – you’re more likely to get hurt.
  4. Even if she says yes but isn’t interested in a second or third date, you’re still going to be more hurt than you would be, perhaps even more so since your hopes would probably have grown by your initial success.

I once said yes to a date with a guy who had been interested in me for years. I’d already turned him down once but he asked again a few years later. I said yes the second time, which was probably a mistake. However, I sensed he wasn’t willing or able to let the prospect of going out with me die so I decided to go on one date.

Nothing in my feelings changed towards him, and when he asked me on a second date, I explained that I just wasn’t interested – but he wouldn’t let it go. He spent a solid 45 minutes batting away my arguments and trying to convince me to go out with him a second time, and I finally relented because he wouldn’t take no for an answer.

Big mistake.

Despite my clear reticence, he was buoyed by his success, and took it very much to heart when I explained to him (again) after Date 2 that I just wanted to remain friends.

Now this shouldn’t have come as a surprise. All the signs were there – my initial rejection, my reluctance, my stated lack of interest and subsequent rejection – and yet he’d built up the idea of me in his mind to such an extent that when I finally made it completely clear that I wouldn’t go out with him again, he couldn’t deal with it.

In the end I think he got hurt far, far worse than he would have if he hadn’t built up the idea of asking me out to such an extent.

Now, I know it isn’t easy asking a girl out. I know you often (if not always) put your heart on the line and risk a not-insignificant amount of pain if you’re rejected. But there’s also no reward without risk.

Putting yourself out there, making yourself vulnerable, is a very good thing. We wouldn’t grow as human beings if we didn’t do this. Incidentally, Brené Brown has some really good talks on this. She’s definitely on the left politically but what she has to say about courage and vulnerability is solid gold.

To quote a point the hosts made on the episode I did for This Catholic Life, if a man can’t display courage and vulnerability in asking a girl out, how can he expect to protect his family later on when necessary? Displaying this kind of courage is a signal to a woman that you’re prepared to take care of her.

Sure, she might turn you down, but that doesn’t mean she doesn’t appreciate that you asked. It could just be that she doesn’t think you’re compatible, or maybe she’s interested in someone else, or maybe she’s been advised to stay single for a time, or a thousand other reasons. I won’t say don’t take it personally, because it is. But try not to take it too much to heart, either.

Now, it’s not okay for women to be mean, condescending or dismissive in turning you down either. This shows an immaturity and a smallness of spirit, and honestly, you should thank your lucky stars you dodged that bullet, even if it really hurts at the time.

So how should you approach dating (or courting, if that’s more your bent)?
Like it’s not a big deal. Because it’s not.


It’s a cup of coffee. Or a meal at a restaurant. Or a few hours at a festival. That’s it.

Here’s a rule of thumb: if you’re attracted to a single young lady, get to know her and, if you think you’ve got a shot, ask her out as soon as it’s appropriate (i.e. not the first time you speak to her).

How do you know if you’ve got a shot? This one is tricky. Generally, if she remains willingly in your conversation for more than five or ten minutes, that’s a good sign. If you find yourself talking to her one-on-one often, that’s another good sign. If she frequently engages you in conversation, that’s a very good sign.

If a woman enjoys a man’s company, she will generally linger. If women are not interested they will usually try to leave the conversation by making excuses, e.g. about needing to use the bathroom, or speak to a friend, or that she needs to go.

If this happens every time you speak to her, it’s likely not a good sign.

But once you’ve ascertained that you might have a shot, don’t procrastinate. Ask her out before you have time to get too attached to the idea of going out with/courting her. Then if she says no, it won’t hurt nearly as much – and you’ll have a better chance of success if you come across mild rather than intense.

Just remember that it’s not a big deal if she says no. She may come round, she may not. Ultimately it’s all in God’s hands. Put yourself out there, but also remember to trust in Him. Because at the end of the day, that’s what is most important.

11 thoughts on “Asking a girl on a date is not a marriage proposal – don’t treat it like one

  1. I think its good advice though for both parties. Although yes it’s been told that coffee is just coffee (etc), perhaps both parties should be told, just go out and have fun! And don’t expect a ring to be produced at the end of the date 🙂

    Liked by 1 person

    1. Alyssa I think both yourself and Anna are pretty much on the money with the advice. Guys just need to place the focus on getting to know their date . I’m no expert but I guess keeping it light and just endeavouring to make it a pleasant experience that could possibly warm the flame of friendship ,that at least is a nice place to be. If I could put it another way- a guy who climbed Mt Everest put the tackling of life’s challenges like this- instead of worrying about climbing the thing in one hit with all the complexity that ,that entails,”man it feels so much better when you drop the expectations and just focus on one step at a time- in other words just enjoy the experience. Remember getting along is a two way street, a good woman will generally coax the conversation along if the guy is nervous- As Anna said women are intuitive.Ps what is fUn?


  2. “But once you’ve ascertained that you might have a shot, don’t procrastinate. Ask her out before you have time to get too attached to the idea of going out with/courting her.”
    This is hilarious. This is is exactly what cads do, ask out without any intention of getting too attached or “courting”. It’s a feature of what they do, not a bug. So that’s what women want…hilarious. Incentives drive behavior…
    If you don’t want to be courted, well, then you’ll get guys who don’t want to court…
    It’s funny to see the lessons we fathers need to teach our sons. You need to be cad-like, cause if you show any signs of courting, you’re rejected. To all parents of sons, there is a lesson here…


    1. I could well be wrong but I think Anna was looking down the barrel with spontaneity being forefront of mind here. I think this advice is premised on the idea of avoiding a date laced with awkwardness because of preconceived notions and expectations.If you like coffee ,lets do coffee, hey yeh,OK

      Liked by 1 person

  3. Yes. Sometimes asking a girl on a date really is a marriage proposal. One of my longtime acquaintances got married today. On their first date his wife actually talked about getting married. That would’ve made me run for the hills. But he wasn’t afraid, because he really wanted to get married. She did too, and he was willing to follow her lead. If I remember correctly, after a month or two into their relationship, she was already talking about an engagement ring. Definitely not my kind of a relationship. Whatever I guess.


  4. The problem is her advice is implicitly rewarding those men whose strongest characteristic is “spontaneity being forefront of mind here”. Guess who those guys are? The men who are happy to hit it and quit it.
    And it looks like you’re also showing the same attitude. Remember, incentives drive behavior.
    But ultimately it’s not about you or Anna. It’s about what women seem to want these days. The lesson for us fathers of boys is teaching them avoidance of “a date laced with awkwardness because of preconceived notions and expectations.” Well, what you’re telling us is our sons don’t need any preconceived notions and expectations of courtship and seriously looking at marriage, but just to go with the flow. Well, like I said before, incentives drive behavior.
    In a more reasonable world, this would mean women would need to rethink what they are doing, maybe with grandma wacking them over their heads with an umbrella for their stupidity. But women being women, it means us fathers teaching our sons what really works with women…revealed preferences.
    Google those last two words…


    1. There was a husband and wife and they were both on safari in Africa. The husband turned to the wife and said” Darling there’s a cheetah over there chasing a gazelle, and I think it’s going to catch it and kill it”, to which the wife replied ” well if it does I’m going to make love to you every waking moment for the rest of your life”. I hope you don’t consider the scenario profane it was just meant to be a bit lighthearted fun.


  5. Mate I would like to answer this at different levels and in several parts. Firstly my heart tells me there is nothing wrong with guys or girls for that matter being comfortable in each other’s company- smiling and laughing and enjoying someone’s company are not sinful acts- nor is sharing a harmless coffee as far as I’m aware. I can’t specifically speak for Anna but this is what I suspect she considers to be the spontaneous act of living life ,I guess in its fullness. Friendship and love are never guided by or seek out selfish motives. This brings us to Jesus specifically. If my heart is coupled to my intellect and serves me correctly, being spontaneous is exactly what Jesus did and excelled at-or put another way,he ditched the script(the law)and from that point on ,life was to be lived according to the heart, and never as far as I’m aware did he scam, mislead or lie to people- in fact his honesty(spontaneity) cost him dearly and in the end his life, because he refused to be scripted by the nonsense of the law(preconceived ideas). Remember we are human not robots,we have feelings,vulnerabilities and we make mistakes. I do realise your reply has embedded complexity and this is my initial response.


    1. “life was to be lived according to the heart”
      Boy, talk about idolizing the heart. Have you never heard it said: “The heart is deceitful above all things, and incurable; who can know it? ” I shouldn’t be surprised…worship of the “heart” is typical these days particularly with women. I mean, it’s just words from Jeremiah…we all know what a bummer he was complaining about everything.
      “Remember we are human not robots,we have feelings,vulnerabilities and we make mistakes. ”
      Yeah, that’s true, but the prodigal son wasn’t a robot, and he lived a life indulging in feelings, and making mistakes along the way. At rock bottom, at least he repented. I see very little of that in these posts and responses. I mean, Jesus was just so spontaneous, it’s not like he had a plan for salvation from before the beginning of time. He just went with the flow…
      The reality is you don’t want to think of your actions, but revealed preferences will ultimately show what you really value. “For where your treasure is, there your heart will be also.”.


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