Why does asking a man out on a date always have to end in tears? Jo Wilding investigates this last bastion of male dominance.


My friend, a self-proclaimed feminist, has just told me it feels like the girl he’s seeing is the one in the driving seat.  This is the same friend who once said he thought it was ridiculous that the man was expected to always make the first move; and that he would love it if a girl took the initiative and asked him out.  I clung to his words, hoping against hope that this was the voice of the future, heralding gender equality in perhaps the last bastion of male dominance in the Western world: the dating game.

Fraught with double standards, and etiquette harking back to a time when men were the breadwinners, I give you less a game, more a farce.  Under questioning, Feminist Friend cracked, saying that, whilst he always hopes to get lucky on a first date, he would probably think less of a girl for sleeping with him so early on.  And as for then having a relationship with her?  Forget it.  (Feminist credentials rapidly wearing thin here.)  A girlfriend, on the brink of a successful advertising career of which Mad Men’s corseted characters could only dream, had me seething with rage when she admitted to expecting her dates to pay for dinner.  Cherry-picking much?  Since having that conversation, I have offered to pay my way with more conviction.  As our Visa cards rubbed shoulders on the salver the other night, my date remarked ‘this is very modern’.  The way it should be.  But it won’t be, so long as we continue to regard being paid for as a sign that the man values our company; and, conversely, take it as a slight when he suggests splitting the bill.  It’s easy and tempting to romanticise the gesture of being paid for as a chivalrous act, but it only works one-way.  How do we pay the same compliment to a man without causing offence?

But before you get to the night of the date, someone has to pick up the phone and do the asking out, a role which invariably falls to the man.  Ringing is a thing of the past.  Nowadays we text, an altogether more dissatisfying method of communication, devoid of tone and susceptible to severe delays.  All the more reason not to wait; instead, we could take it upon ourselves to go out on a limb, risk rejection, and ask the guy out.  Hmm I think I lost you at rejection.

When I stop to analyse why I think it is best not to initiate, this is what I come up with: it takes a greater level of interest on the part of a guy to move him to act, to make a move, than it does a girl.  I don’t mean that he is lazier about these things, rather that he is, generally-speaking, less preoccupied with romantic matters.  Byron’s famous lines come to mind:

Man’s love is of man’s life a thing apart,/ ‘Tis woman’s whole existence.

If a man goes to the trouble of asking a girl out, he is very interested, an essential ingredient if the relationship is to flourish and go places.  If on the other hand the girl is calling the shots, making things happen, in the driving seat, eventually the car will leave the road, or stall.

Whenever I’m tempted to break the rules and ask a man out for a drink, I recall the times that I’ve done just that, only for it to end, if not in tears, in the pudding section of my nearest supermarket.  And so, unless I can think of a convincing enough reason why they might not have got in touch (and I do a mean line in these), I step away from the phone.

But the question still remains: why should the guy taking the initiative continue to be the status quo?  ‘Because they need to know they’ve won us!’ a girlfriend says over lunch, as if it were a statement of the bleeding obvious.  ‘If you make the first move, it implies that you’re in some way inferior to them,’ and you don’t want them thinking that; you’ll be devaluing yourself in their eyes.  Men are born hunters, motivated by competition and the chase.  As such, we must remain elusive, mysterious, and, so, desirable.  She then asks, as if this is going to seal the deal: ‘You’ve read The Rules?’  Yes, and thrown it across the room; and picked it up again.  The consensus round the table (four female Oxbridge graduates, two trainee lawyers amongst them) is that The Rules: Time-Tested Secrets for Capturing the Heart of Mr. Right (be a creature of mystery, never ask a guy out, play hard to get etc) contain more than a kernel of truth, however loathe we might be to admit it.  When I confess to having asked guys out in the past, I am asked in a less-than-flattering tone:

‘Did any of them say yes?’

We laugh.

‘Yes, but it didn’t go anywhere.’

And there it is, the association of two things, the woman making the first move, and the ensuing dating not going anywhere, which might not be connected, but which social norms lead us to think probably are.  Mess with the status quo, and you’re asking for trouble.  As Feminist Friend’s reaction suggests, even those guys who want to be asked out don’t really want it.

The social conventions which govern dating are all about value.  The onus continues to be on the man to ask the woman out, to pay for dinner, and to initiate kissing/sex.  If a woman does any of these things, she is effectively devaluing herself.  Who knows, one day the tides may turn, and the woman who takes the initiative will instead be seen as self-assured and confident, and all the more valuable for it?