Making conversation on the spot

TOneThousand

Don Juan
Joined
Nov 10, 2023
Messages
19
Reaction score
10
Walking by a cute girl and she says "hey nice shirt". You say "thanks I got it at target". She laughs and says "target has the best shirts". You say something funny about target being really high quality.

That's the end of the discussion, which is not great. How do you guys turn that into a real interaction/make real conversation? Do you always have something generic to ask them or something canned that will lead to back and forth? Feels like having some sort of "can you believe this topic of the day" ready to go is the most obvious way to do it. Basically be ready to ask a question to anyone that they'll have to engage on.
 
Joined
Aug 4, 2023
Messages
5,127
Reaction score
4,306
That's the end of the discussion, which is not great. How do you guys turn that into a real interaction/make real conversation? Do you always have something generic to ask them or something canned that will lead to back and forth? Feels like having some sort of "can you believe this topic of the day" ready to go is the most obvious way to do it. Basically be ready to ask a question to anyone that they'll have to engage on.
You took the wrong approach, I think. The shirt remark is her opening you, don't make the shirt the topic of discussion.

Walking by a cute girl and she says "hey nice shirt". You say "thanks I got it at target". She laughs and says "target has the best shirts". You say something funny about target being really high quality.
Don't take anything a woman says at face value. She's not complimenting your shirt, she complimenting your taste. A smart seducer would bounce back to tell her she has good taste, go on talking about taste, et cetera.
 

pipeman84

Master Don Juan
Joined
Aug 21, 2022
Messages
1,356
Reaction score
1,797
Age
39
Location
Europe
Walking by a cute girl and she says "hey nice shirt".
The chances of this actually (her being cute and really a girl (early 20s) not a 45yrs old woman, not part of a dare, TikTok trend etc) happening to a guy in OP's age range (+38yrs old) must be on par with finding a suitcase full of $100 bills on the street.
You say "thanks I got it at target". She laughs and says "target has the best shirts". You say something funny about target being really high quality.
That's the end of the discussion, which is not great. How do you guys turn that into a real interaction/make real conversation?
I'd say something like 'so, who are you? what's your story?'. That's pretty open ended and can start discussion in all sorts of directions.
 

Vending Machine Veteran

Senior Don Juan
Joined
Mar 30, 2024
Messages
214
Reaction score
135
Age
39
Walking by a cute girl and she says "hey nice shirt". You say "thanks I got it at target". She laughs and says "target has the best shirts". You say something funny about target being really high quality.

That's the end of the discussion, which is not great. How do you guys turn that into a real interaction/make real conversation? Do you always have something generic to ask them or something canned that will lead to back and forth? Feels like having some sort of "can you believe this topic of the day" ready to go is the most obvious way to do it. Basically be ready to ask a question to anyone that they'll have to engage on.
That sounds too good to be true.

When I was cold-approaching i had canned questions, yes.

I'd start with something funny, like "is that shirt from Target?"

Her: blah blah

Did you steal it? That looks like a price tag *prerends to look where a price tag would be*

Then I would go into the canned.

"What's your name?" "You look like a tourist" "oh wow"

You have to practice talking to people to know what to say. It can't come out of a book or forum
 

Vending Machine Veteran

Senior Don Juan
Joined
Mar 30, 2024
Messages
214
Reaction score
135
Age
39
Your demeanor means more than anything you could say.

Acting natural, with a hint of condescension works wonders.

Problem is, you actually have to practice to get good at this. And most people won't

Proper preparation prevents poor performance
 

SW15

Master Don Juan
Joined
May 31, 2020
Messages
12,608
Reaction score
10,713
Always start with asking an open ended question and see where the conversation goes. Keep asking her questions and see how willing she is to participate in a conversation.
 

Divorced w 3

Master Don Juan
Joined
Nov 20, 2022
Messages
2,338
Reaction score
1,279
How about thanks nice ass?
 
Joined
Aug 4, 2023
Messages
5,127
Reaction score
4,306
I think you mean ask her an open ended question such as, so are you a working girl in your free time?
"How is Only Fans working out for you?"
 

TOneThousand

Don Juan
Joined
Nov 10, 2023
Messages
19
Reaction score
10
@SW15 open ended questions, yes that's a good call man. Basically you should always have open ended questions ready. Thanks!

@AmsterdamAssassin good point about the comment not being about the shirt and really being about taste. I get what you mean about turning it back on her and talking about her taste

@Vending Machine Veteran thanks, yeah practicing some conversation with the right demeanor and some condescension is a good call

Obviously who doesn't like a good white crop top!
 

BeExcellent

Master Don Juan
Joined
Dec 16, 2015
Messages
4,666
Reaction score
6,566
Age
55
Walking by a cute girl and she says "hey nice shirt". You say "thanks I got it at target". She laughs and says "target has the best shirts". You say something funny about target being really high quality.

That's the end of the discussion, which is not great. How do you guys turn that into a real interaction/make real conversation? Do you always have something generic to ask them or something canned that will lead to back and forth? Feels like having some sort of "can you believe this topic of the day" ready to go is the most obvious way to do it. Basically be ready to ask a question to anyone that they'll have to engage on.
Advice from the old lady:
Her: "Target has the best shirts..."
You: "Hmmm. They do. I like that you are a practical gal....."

Conversate from there.
 

mikedee

Master Don Juan
Joined
Jun 26, 2022
Messages
789
Reaction score
891
Walking by a cute girl and she says "hey nice shirt". You say "thanks I got it at target". She laughs and says "target has the best shirts". You say something funny about target being really high quality.

That's the end of the discussion, which is not great. How do you guys turn that into a real interaction/make real conversation? Do you always have something generic to ask them or something canned that will lead to back and forth? Feels like having some sort of "can you believe this topic of the day" ready to go is the most obvious way to do it. Basically be ready to ask a question to anyone that they'll have to engage on.
Go direct
 
Top