A Lover’s Guide to How to Smoothly Approach a Woman When Cupid’s Arrow Strikes

'The Temptation' image
‘The Temptation’ by Paul François Quinsac (1858-1929). Image from ‘Salon Illustré’ (1888)

No need is there of talking on the hand;
Nor nods, nor signs, which lovers understand.
But boldly next the fair your seat provide;
Close as ye can to her – and side by side.
Pleas’d or unpleas’d, no matter, crowding sit;
For so the laws of public shows permit.

– Ovid, ‘Ars Amatoria’ I, transl. John Dryden

As Ovid observes in his Ars Amatoria (Art of Love), at least in the words here of Dryden’s translation, ‘Cupid, indeed, is obstinate and wild’. The mischievous god takes aim and fires his darts without any warning … and often at the most inconvenient times and places.

Here at Cupid’s School then, we’re going to prepare to make a move and meet a nymph when Cupid’s arrow has struck. This then is the first post in our series on seductive social skills and How to Engage a Woman You Want in Seductive Conversation.

So now, let’s imagine again for a moment you’ve spotted a beauty who takes your fancy. And, ouch! You’re still reeling from the dart. She could be sauntering along the street, sat sipping a modern coffee concoction, swanning around a shop, or in any one of numerous situations. Chances are, though, you’ve got some work to do before you can even open your mouth and speak.

Of course, each situation will be different. But, broadly speaking …

You’re going to find yourself in one of two basic situations

1) Close enough to talk

The gods have been kind, perhaps, and circumstances have brought you both close enough to simply engage her and start a conversation there and then.

Here are some examples:

  • She’s standing behind or in front of you in a queue, like at a bus stop or in a café or a shop.
  • She’s sat or standing near you in a café, a bar, or any other environment where people are sat or stood close together.

2) Not close enough to talk

You see her but aren’t close enough to engage her and start a conversation. Clearly then, you’re going to have to approach and get close enough to speak.

Here are some examples:

  • You see her walking along the street or browsing in a shop.
  • You see her in a café, a bar, or any other environment where people are sat or stood close together, but you’re not close enough to speak.

Now, far more often than not, you’re going to find yourself in the second situation. That means you’re going to have to approach her first to get her attention and engage her. That, my friend, it seems, is how the god’s would have it.

The first challenge then to overcome is how to smoothly approach a woman that catches your eye and lights your fire when you’re not already close enough to talk.

So then, you could find yourself in any one of numerous situations when you see her, and Cupid strikes. The specific logistics of the situation, meanwhile, will influence your choice of approach. But essentially …

You have two options to choose from

1) The indirect approach

Basically, with the indirect approach, you employ an excuse, like something in the environment, to get close enough to engage her in conversation, i.e. to get into situation one. The good thing about this is that it’s a low pressure approach for both of you. It gives you both the opportunity to talk and get a feel for each other without any expectations or attracting much attention, which she – and, indeed, you – might find intimidating.

So, the good news is …

The environment you’re in will often provide opportunities for you to engineer, as if by chance, a situation where you’re close enough to talk.

Here are some examples:

  • You’re sat in a café and see her walk in and join the queue. In this case then, it can be as simple as just getting up to join the queue behind her.
  • You can do the same if you’re in a shop and see her join the checkout queue.
  • Or, maybe you see her browsing the stands in a shop. You can get close enough to talk then by going to check out something on the shelf where she’s looking.
  • Or, maybe, you see her when you enter a café, a bar, or some other similar environment. If you see her sat there with a seat available next to or close to her, then that’s where you’ll need to go and sit.
  • If you see her in a café, a bar, or some other similar environment, but can’t get to sit close enough to her, look around for some other excuse. Are there any interesting pictures on the wall near to where she’s sat? Are there any unusual or otherwise notable objects nearby you can go to look at and employ as a pretext to start a conversation?

2) The direct approach

Sometimes, though, you’ll see a woman but won’t be able to make an indirect approach to get close enough to start a situational conversation, at least without behaving like a stalker. You might, for example, see her walking down the street, in front of you or coming towards you, and she’s not just browsing. Meanwhile, she’ll be gone, and you may never see her again, if you don’t approach her directly and tactfully interrupt her right away.

In these situations then, you could just walk, or run, right up to her and communicate your interest and desire to get to know her, right from the start, with an explanation and a well-chosen compliment. This can, at times, be a potent way to start.

This direct approach, however, can put more pressure on you both, and, perhaps, especially her if she feels she can’t easily get away without appearing rude. It may also trigger some socially conditioned resistance, which an indirect approach might have been able to circumvent.

What’s more, you’ll want to consider how the environment you’re in and the wider social situation are likely to affect her and impact your interaction. If a particular busy environment is likely to be a problem, you can give some thought to how you might make your direct approach more discreet. You could, for example, wait until she leaves the café or gets off the bus before you approach her then – or, even, perhaps, prepare to slip her a charming note, or a sort of mini love letter, with tactful prayer-like call to action.

If you make a direct approach and stop a woman in the street, just be sure not to behave like a street seller or one of those charity fund-raisers. In short, you’ll want to stop her much like you’d stop someone to get directions or to return something she dropped or left behind. They key here then is to get her to stop and engage with you, but without scaring her or causing her to think you’re selling something or the like.

Creative genius

So far then, I’ve shared what you might call the rudiments of pick up. This, though, is an example, I think, of creative genius:

I felt a great temptation to address a few words to the beautiful girl, but I was afraid she might run away and never come out again; however, unable to control myself any longer, I determined to write to her; I had no difficulty in conveying the letter, as I had only to let it fall from my balcony. But she might have refused to pick it up, and this is the plan I adopted in order not to risk any unpleasant result.

Availing myself of a moment during which she was alone in the yard, I dropped from my balcony a small piece of paper folded like a letter, but I had taken care not to write anything on it, and held the true letter in my hand. As soon as I saw her stooping down to pick up the first, I quickly let the second drop at her feet, and she put both into her pocket. A few minutes afterwards she left the yard. My letter was somewhat to this effect:

“Beautiful angel from the East, I worship you. I will remain all night on this balcony in the hope that you will come to me for a quarter of an hour, and listen to my voice through the hole under my feet. We can speak softly, and in order to hear me you can climb up to the top of the bale of goods which lies beneath the same hole.”


At midnight, as I was beginning to give her up, she came forward. I then laid myself flat on the floor of the balcony, and I placed my head against the hole, about six inches square. I saw her jump on the bale, and her head reached within a foot from the balcony. She was compelled to steady herself with one hand against the wall for fear of falling, and in that position we talked of love, of ardent desires, of obstacles, of impossibilities, and of cunning artifices.

– Jacques Casanova de Seingalt, ‘The Memoires of Casanova’, trans. Arthur Machen

Now, there’s some timeless literary inspiration, and food for thought, for developing a more creative approach that’s suited to a unique situation with its own particular challenges.

And so, now you’ve approached her and got close enough to speak. You’re learning to make things happen. But before we move on to what to say and before you open your mouth, let’s not forget it’s not just what you say but how you say it as well.

The next post in this series then is A Lover’s Guide to Seductive Non-Verbal Communication – to Make a Potent First Impression …