A Lover’s Guide to How to Smoothly Start a Situational Conversation When Cupid’s Arrow Strikes

Image of race-day at the Circus Maximus
Race-day at the Circus Maximus, where a lover could be found. Image of ‘Chariot Race’ by Alexander von Wagner (1838-1919) from ‘Roma: Ancient, Subterranean, and Modern Rome, in Word and Picture’ (1916) by Albert Kuhn (1839-1929)

Then find occasion to begin discourse;
Enquire whose chariot this, and whose that horse?

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

In the previous post in this series on seductive social skills, we broadly considered how to start a conversation with a woman in any one of numerous situations. In this post then, we’re going to focus now, in particular, on how to smoothly start a situational conversation.

So, let’s go back again and imagine. You’re sat or stood now next to this delightful child of Venus. The gods were kind, perhaps, and put her in your way. Or, maybe, you spotted her from a distance and approached her indirectly, to discreetly get to meet her. And now it’s time to speak.

In this post then, you’re going to prepare to open the interaction. More specifically, you’re going to learn how to generate and use a situational conversation starter to initiate a potentially seductive interaction with the woman who takes your fancy.

The situational conversation starter

I introduced a brief definition of a situational conversation starter in the previous post in this series. But now, for the sake of clarity, here it is again:

A situational conversation starter is when you start a conversation by addressing someone (in this case a woman) with a remark, a question, or both about something in the environment or situation you’re in.

The good thing about a situational conversation starter is it’s a flexible, low pressure way of initiating a conversation. You can spontaneously generate one on the fly and start getting a feel for each other without any pressure of expectations or drawing much attention to yourselves in a busy environment – which either or both of you might, otherwise, find somewhat disconcerting or indiscreet. In the first book of The Word of Venus Art of Love, meanwhile, Ovid himself advocates employing a situational conversation starter whilst at the races, or the Circus Maximus, in ancient Rome.

If, however, you’re still into her once you’ve started the conversation and chatted a bit, you can start being more direct, or open, then or, otherwise, start obliquely indicating your interest and intentions, as Ovid does at the races in the first book of his Ars Amatoria (Art of Love). That way you’ll promptly set an amorous context and not be considered just a friend. In other words, you won’t fall into what’s often called ‘the friend zone’. Instead, you’ll set a seductive or amorous context to the interaction, more or less, from the start.

After you’ve chatted a bit then, you might openly confess, for example, why you initiated the conversation. Or, you might, instead, just demonstrate your amorous interest with your chivalrous attentions and amorously courteous non-verbal communication, whilst you engage her then in seductively attentive conversation.

How to smoothly start a situational conversation

You can think up a unique situational conversation starter on the fly and then spontaneously initiate a conversation. All you have to do is ….

Identify some aspect of the environment or situation you’re in and then address her by commenting on it, asking a question about it, or both.

Here are some basic examples then of situational conversation starters:

  • ‘Whose chariot is this? Whose horse is that?’ (Ovid at the races, or the Circus Maximus, in ancient Rome)
  • ‘You look cheerful. Has it been a good day?’
  • ‘You look like you’re from somewhere exotic.’

5 ways to help you master the art of the situational conversation starter

1) Develop your powers of observation

The key to starting a conversation this way is to be observant. Pay attention then to the details of your environment and what’s going on around you.

Here are some examples:

  • What’s the weather doing?
  • What are the other people around you doing?
  • What aspects of your environment are intriguing, funny, or otherwise remarkable?
  • What’s the woman doing?
  • What are you doing?
  • What’s intriguing, funny, or otherwise remarkable about the way she looks or what she’s doing?
  • How’s she feeling and why? Are there any remarkable clues on her face or in her actions?
  • How are you feeling and why?

There’s an abundance of sensory data coming to us at any particular time, in the form of sights, sounds, smells, tastes, and feelings. So, practise becoming more aware of these details and then using them as raw material for starting conversations. With practise, you’ll get better and quicker witted then at generating conversation starters on the fly in all sorts of situations.

What’s more, this sort of heightened awareness can also help you cultivate your character. It can enrich your experience then, make you more perceptive, and provide an abundance of food with which to feed your wit and thus your charm.

2) Try to enter the conversation she’s having in her head

There’s a concept in sales and marketing that’s often used to engage the attention of potential customers. And, this can work well with conversation starters too. The idea then is to first understand the conversation that’s already taking place in the potential customer’s head. Then, the sales pitch is begun by entering this conversation to engage the person with less resistance.

So, when you see the girl you want to talk to, you can look for clues about what she might be thinking and how she might be feeling. If you can demonstrate this sort of attentive empathy when you open your conversation, you’ll be able to slip nicely then into her train of thought and then begin to move things on from there.

3) Do it different

If you can make your conversation starter a little more original and different to the norm, like more perceptive or funny, all the better. You might use your imagination then to humorously exaggerate, misinterpret, or reinterpret things. You might, at times, like to play the fool a bit and ask some silly or outlandish questions instead about situational things.

Don’t worry, though, if you can’t think of anything that special on the spot. If that’s the case, just be boldly banal. Your non-verbal communication and overall vibe are usually more important anyway than what you actually say.

4) Be curious and dig a bit deeper

Another way to generate alternative and, perhaps, more interesting conversation starters, and food for discussion, is to take something in the environment or situation and employ Rudyard Kipling’s ‘six honest serving-men’ to dig a bit deeper and come up with ideas:

I keep six honest serving-men
(They taught me all I knew);
Their names are What and Why and When
And How and Where and Who.
I send them over land and sea,
I send them east and west;
But after they have worked for me,
I give them all a rest.

Try it when you’re out and about and see what ideas you get.

5) But don’t get stuck in your head

Often, though, it’s more important here to just open your mouth and speak as soon as possible, even if it’s just ‘hi’ at first. The longer you stay there not saying anything, and stuck in your head, the more awkward it’s likely to feel to start.

If you can’t think of anything else then, you can simply smile, assume some rapport, and say ‘hi’, and then begin with a small talk question or comment.

Here are some examples:

  • ‘How are you doing?’
  • ‘You look like you’re enjoying yourself.’
  • ‘This place is great.’

Then, follow up by engaging her in conversation …

So then, now you’ve learnt to create a situational conversation starter, you’re going to be able to initiate casual conversations with women in all sorts of situations. You’re going to have more options and be able to make things happen.

Having opened the conversation, however, it’s time now to move the interaction on with some scintillating small talk. But, before we do, we’re going to turn our attention, in the next post in this series, to how to initiate a conversation with a woman directly with a compliment. You’ll be prepared then even for circumstances in which you’re unable to start a situational conversation.