‘Are we actually dating?’

I mentioned in my last post that this was an issue that I wanted to address, as it is all too common in our world.

Regardless of your opinions regarding dating vs courting, the fact of the matter is there is often too much ambiguity surrounding romantic intentions, so much so that it can be unclear whether the other person sees you as ‘just a friend’ or something more.

This is arguably a direct result of the development of the modern dating culture, however since this is the culture we’re in (and I’m not convinced how realistic ‘courting’ in the traditional sense is these days) I think this ambiguity is something that needs addressing.

I have lost count of the number of times I’ve heard women say something along the lines of “I don’t know if we’re actually dating or not”.

I’m not too sure if this goes both ways. I imagine it must, at least on occasion, but it does primarily seem to be an issue women have with men.

I don’t quite know when this all began – presumably along with, or sometime after, the sexual revolution. The modern ‘casual’ nature of secular dating has trickled into our own Christian spheres, with many men in the Church now appearing reticent about declaring their intentions when pursuing a lady. My sense is that this comes from a fear of rejection or a subconscious imitation of the example set by our non-Christian peers or some combination of the two, and probably other factors besides.

A few years ago I bumped into a young man I’d known for some years at a wedding; afterwards he started contacting me, and asked if he could come by for a coffee or a beer. We had good chats but he never mentioned dating (or courting for that matter) or anything specifically romantic. This happened a couple of times – with me not really certain what this was or where it was going – until he asked if I’d like to have dinner.

So I asked him directly, “is this dinner as friends or is it romantic?”

He looked me square in the face and said, equally directly, “no, this is romantic”.

While a bit taken aback, I was pleased by his directness; but up til that point I wasn’t sure what his intentions were. I’ll admit part of my confusion was due to conflicting advice I was receiving from mutual friends – some saying his attention was clearly a romantic pursuit and others telling me he had several female friends and often spent time with them, and this was nothing more than that.

It’s also worth mentioning that I did catch up with this guy one-on-one a couple of years earlier without getting any impression of romantic interest or pursuit, which added to my confusion.

Now, I don’t think this guy was either being deliberately reticent or following the ‘casual dating’ example of others. I think, in his mind, he was very obviously pursuing me in a romantic way, but because of our friendly history, and his lack of verbal clarity until directly asked, I was confused. To his credit, he made things 100% clear when asked, but it seems a bit odd to me that I needed to ask at all.

I’m not really interested in dissecting how we got here, or who is at fault, etc, but rather, in giving some advice which will hopefully help overcome this sort of ambiguity.

So here are my top tips to avoid ambiguity in dating (or courting).

For Men:

  • If you’re interested in pursuing a girl, make your intentions clear at the outset. If you’re not sure how, questions like these will help provide clarity:

    May I take you out sometime?/I’d like to take you out sometime, if that’s alright with you?

    Can I buy you dinner/a drink?

    Could I buy you a coffee sometime?
  • Assume you’re paying for the meal (or whatever you’re doing), at least on the first date. Going Dutch or expecting her to pay for herself is a big signal to her that this may not be a date after all, or that you’re not keen. A decent woman will appreciate the fact that you’ve paid, as it’s the mark of a gentleman.
    N.B. If she insists on paying for herself, it could be that she’s being overly polite, or it could be a sign that she’s not interested in you or perhaps that she’s an intense feminist and really believes in taking that equality thing the full gamut. To ascertain which, gently insist that you want to pay for the meal. If the former, she will usually relent. If either of the latter, ditch her – it won’t work out.
  • Never, EVER ask a girl out by using any of the following phrases (unless you’re a teenager and have no intention of seriously dating):

    Do you want to hang out?

    Let’s catch up sometime.

    Some friends are going to see this movie. Want to come with?

    This is Ambiguity Central. If you really want to confuse her about your intentions, any of these phrases will do the trick.
  • Make it clear you’re keen on her. This one is for after the initial getting-to-know-you stage. Don’t play it cool, Mr Nice Guy. She wants to know if you think she’s pretty/fun/cool/talented/intelligent – or all of the above – so tell her! You don’t have to be Shakespeare. It could be something as simple as you look beautiful tonight when you meet her.

    Don’t just use your words, either. Bring her flowers – I don’t know a woman who doesn’t love to receive flowers. Obviously, don’t overdo it either; a compliment each time you see her and flowers after you’ve been on 3 or 4 dates is appropriate.
  • Ask her about herself. A woman I know recently went on a date with a mutual friend. When I asked her how it went she shook her head in exasperation and told me he spent a solid hour talking about himself and didn’t ask her a single question about herself. Not one! Everyone enjoys talking about themselves – just remember to use this to your advantage when taking a girl out.
  • If you’re not keen, don’t spend one-on-one time with her. Sometimes the problem is not that a man has failed to make his intentions sufficiently clear, it’s that he’s not interested at all but still ‘hangs out’ with the woman. Unless you have a very, very clear friendship and mutual understanding, you shouldn’t be spending solo time with any single woman. It causes a huge amount of confusion for her about why you’re spending time with her, especially if you don’t know each other well. If you want to ‘hang out’, do so in a group or not at all!

For women:

  • If in doubt, ask. If you’re really not sure whether you’re dating the guy or not, just ask (see my story above). Early disappointment and a bit of embarrassment are far better in the long run than living in the agony of doubt and confusion, dashed hopes and ultimate humiliation. Not sure how to ask? Try one of the following:

    Are we just friends or is there something more going on here? Because I’m a bit confused.

    Are you asking me on a date or are we just hanging out as friends?

    I’m not sure what you’re asking me. Can you please make it clearer?
  • Make it clear you’re keen on him. Men need encouragement, just like we do. This can be done through something as simple as smiling. Ask him questions about himself (this is a two-way street). If you’ve been seeing each other for more than a few weeks, try to take an active interest in his pursuits, even if they don’t seem very interesting to you. He will appreciate this and it’s a good sign you’re interested.
  • Reward his chivalry. If he is trying to be a gentleman by paying you compliments, holding open the door for you, paying for your meal or otherwise, smile and say “thank you”. This is not the time to assert your equality! Recognise that it takes guts for men to do these things, especially in today’s culture in which they might be lambasted for simply trying to show a woman respect. It doesn’t matter whether you’re keen on him or not, this kind of behaviour should be encouraged. If you laugh at him for holding open a door for you, you’ve just crushed his masculinity and humiliated him in one fell swoop, as well as ensured he thinks twice before doing something like this again.
  • If you’re not keen, tell him. Nobody appreciates being messed around with. Fight the fear of hurting his feelings and tell him, kindly, that you’re just not interested. Whatever you do, DO NOT string him along once you know this thing has no future. See this post for suggestions on how to do that.

Any other tips? Comment below!

18 thoughts on “‘Are we actually dating?’

  1. Solid advice Anna! One thing I’d offer in terms of a “how we got here” that may be helpful. Perhaps this was peculiar to my circles growing up as an American Evangelical Protestant, but this phenomenon (which was all over the place) was more about an excessive reaction to casual dating culture than about embracing it (the most prominent face of this thinking incidentally was Josh Harris.) Good Christians, the thought was, didn’t play fast and loose with girls’ hearts. Getting attached before you basically knew you were going to marry the person was cruel because it lead to heartbreak. It could even compromise what was called “emotional” or “heart” purity, regardless of physical chastity. So good Christians didn’t date in the first place. The result was either a highly formalized version of old fashioned courting, or, more commonly, this. A lot of young men I grew up with picked up the habit of “just talking” with a girl, because at least seeming like you were maintaining emotional distance until you were ready to propose had become the standard of propriety. Like I’ve said I don’t know Catholic circles that well, but I suspect this is related to your observations about guys building up for three years to ask a girl out. I regret it now, but I’ve done similar things before when these ideas had a stronger hold on my friends and peers.


  2. Anna what do you mean by a subconscious imitation set by non- Christian peers?Rejections,rejection isn’t it?Is Christian rejection felt more acutely or could the other factors at play,be,being shy or embarrassed or lack of confidence. Could the deep seated subby be the fact that ultimately a guy asking a question is for all intents and purposes fronting up and asking for someone they like to pass judgement on them and the whole spectrum of negatives that may potentially entail. I mean Box’s response to one of the outcomes in that podcast was that he felt that ultimately that his rejection was his fault. Peter Holmes shut that route down pretty smartly. I feel that Box’s response is negative self image ,almost at a subconscious sobotaging of self,that to my mind at least leads to introspection, that ultimately can drag the psyche to its base level ,that of being somewhat introverted at that level of confidence-which basically is the default position for flight or fright if you like- all ultimately set in motion to avoid pain at any cost. Your thoughts please! Ps is this why guys anaesthetise their brains by drinking?


  3. Wise words Anna. If I think about my experiences with men (and my friends’ experiences) I can confidently say that “intentionality” is probably the most important important aspect of dating. A man who states his intentions clearly is so refreshing! and clarity is a blessing.
    I wonder if ‘ambiguity surrounding romantic intentions’ is also a symptom of a culture of ambiguity in a general sense. White lies, vagueness and non-committal communication (so as not to hurt anyone’s feelings or to keep one’s options open) seem pretty commonplace.
    I think we as younger adults, both men and women, would do well to embrace clear communication, honesty and frankness – I know I need to work on these myself. Thanks for inspiring me to think about this Anna!

    Liked by 1 person

  4. I kind of agree with all this but with caveats:
    There should be no need for a man to be upfront with his intentions on a first or second date: if he is asking, he is at least mildly interested. The problem is when he tries to mask his intentions by muddying the waters.
    If Christian men are imitating the ambiguity of secular dating it could be because they notice their secular peers actually getting dates while they are home alone.
    One has to be careful about recommending men be chivalrous: what a man imagines is gallant and chivalrous women often find ridiculous and off-putting. The man ends up expending a lot of effort and taking emotional risks with no reward.
    There really are no rules anymore and sticking too close to a script or proposing alternate rules just seems to set people up for failure. Christians who really want to marry have to be very patient with the opposite sex and overlook a lot of awkwardness.

    Liked by 1 person

  5. These are wonderful, Anna. I’d add one more tip for guys: don’t let yourself be strung along. If you don’t get some intentional words back from her reciprocating in the desire to date, see the evening through, thank her for her company, say she can call you anytime, and then move on and don’t think about her again unless she calls you to say she’s decided she’s interested after all. Sure women shouldn’t lead men on, but dammit be a leader and a man and do what needs to be done rather than making her do it for you.


  6. Call me old fashioned,at the end of the day all of this boils down to etiquette (the dictionary/meaning of agreeableness )manners,being courteous, and bring politeness with a well meaning honesty. Sure it sounds stolted and awkwardly stiff,it is what it is isn’t it🎶.


  7. Dating is inherently ambiguous. It really doesn’t matter if people know that they are dating if no one knows what dating actually means. Dating seems to refer to everything from the incontinent fooling around of teenagers to the serious spouse hunting of mature adults, and everyone has different conceptions of what the process looks like and what the expectations are. Even their own conception changes as they age.
    To the extent that dating becomes more clear, it comes to look like courting, just as the Novus Ordo becomes more reverent/beautiful to the extent it greater resembles the Traditional Latin Mass. If the only way to make something better is to make it as close as possible to some other thing, why not just do the latter thing in the first place?

    Liked by 1 person

  8. I think that — at the root of the ambiguity, at least for dudes — is the fear of rejection. In my teens/early 20s, I was definitely petrified at the prospect of being rejected by a girl if I asked her out. It’s really incumbent upon fathers, grandfathers, friends, etc. to help combat this dread: Make it clear that rejection is part of life and of finding the right girl to marry.
    P.S. I still think that there is room for some sort of “guided” approach to spouse-seeking that involves the use of family-wide or parish-wide contacts.

    Liked by 1 person

    1. Carlos I have the opposite problem with women,in that I’m absolutely petrified of someone saying yes because at that point what do I do next- at least in the good old days a Shakespearean script may have helped one appear to take on a semblance of control,to wit ones lack of confidence and imperfections could be masked .If you like the approach type was strong and silent 😃. Carlos as an aside,do you think that maybe as a society we may have failed to inculcate a stronger sense of the value of humour in being a great foil for smoothing out life’s bumps. Humour really is a wonderful gateway to fostering friendship,as it places the whole dynamic into neutral territory and thereby subdues the intensity of human interactions and thus elevates the psyche to the level of engagement -the spontaneous .


      1. I think you’re correct that humor (or humour for you in the Commonwealth 😊) is underrated. In fact, self-deprecating humor, I’ve found, is a great way to make others more comfortable around me.

        Liked by 1 person

  9. > “May I take you out sometime? I’d like to take you out sometime, if that’s alright with you?”

    “If that’s alright with you”? Don’t ever say those words. This is simp nonsense. Asking a woman out should be framed as a statement i.e. “We should go out sometime. There’s a new [restaurant/activity/etc] I’ve wanted to try, let’s go this Saturday night.”

    It’s literally that simple. And if she doesn’t know your intentions while you’re on the date, that’s a WHOLE other problem.

    Either way, never qualify yourself with any of this “if it’s ok with you, if you please, if you wouldn’t mind, m’lady” nonsense.

    *Edited by admin


  10. This is a strange post to see from Hitchings specifically. The author who’s best known for a viral post about how the number of Christian men is in short supply now writes here to object to the wooing behavior of these supposedly missing guys. Together that makes as much sense as advice on how to care for a pet Dodo bird!


  11. I’m not too sure if this goes both ways. I imagine it must, at least on occasion, but it does primarily seem to be an issue women have with men.
    I assure you it does, at least on occasion. As a younger man, I had one or two instances where, even after explicitly using the term ‘date’ in my invitation and being pretty clear about my intentions (and then, of course, paying for the both of us), afterwards the young woman responded to an invitation for a second date with, “Wait, I had no idea that was a date! Oh, I never would have agreed to one of those in the first place.”


  12. Hmmm…. Make your intentions clear. Tell her exactly what you’re thinking. Lay all your cards on the table. Lower your defenses and open the gate. Give her a huge advantage. Completely open yourself to attack. Do for her what she would never, ever, do for you.
    No thanks.
    Men are allowed to not know exactly what they want all the time. Men are allowed to preserve their pride. Men are allowed to wait until they are reasonably confident the interest is mutual. Men are allowed to invite women to spend time with them and see what develops, or not. Women are allowed to accept or decline said invitation. Men are also allowed to decide they are NOT interested, just as women are.
    Welcome to equality. Now I suggest you embrace it. Or are all women hypocrites?


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