How to Talk to Men in on the Street
#2 Conversation Options
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"It's really nice to see someone [reading a physical book/enjoying the quiet/just people-watching]. What's your take on [digital vs. physical books/the city bustle/human behavior]?"
Observing his calm activity and then asking for his opinion shows you're observant and interested in his thoughts.
"This [weather/event/place] is amazing, isn't it? What's your favorite part about it?"
A positive observation about the shared environment, followed by a question that encourages his opinion and personal connection.
"Your [dog/child] is so well-behaved! Do you have any tips?"
Animals are fantastic conversation starters. Most dog owners love to talk about their pets, and it's a very friendly approach.
"This [line/wait] is crazy! What's the wildest thing you've seen happen while waiting for something?"
Turning a shared, potentially annoying, situation into a light-hearted topic can lead to funny stories and bonding.
"I'm actually [new to the area/just visiting]. What's something cool I shouldn't miss around here?"
This invites him to play the role of local expert and share his knowledge, often leading to suggestions and further conversation.
"So, besides [reading/listening to music/waiting], what else are you up to today?"
This directly asks about his plans, showing interest beyond the immediate interaction and inviting him to share more.
"I'm trying to find [a good cafe nearby/the best route to the station]. Do you have any recommendations?"
Continuing to ask for advice or recommendations keeps him engaged as a helpful resource and can lead to more discussion about local spots.
"Do you come here often? I feel like I've seen you around, and you always seem to have interesting [books/outfits/accessories]."
A bit flirty, this acknowledges his presence and implies a positive observation about him, inviting him to confirm or expand.
"I love that [band/author/podcast]! Have you been following them for long?"
If the initial connection was over a shared interest, this deepens the discussion, showing you're genuinely interested in the topic.
"I noticed you were [looking at the map/struggling with that package]. Is everything okay, or do you need a hand?"
Offering help or showing concern for a visible situation makes you appear approachable and kind, creating a natural entry point.
"What brings you to [this part of town/this park] today?"
A broad question that lets him share as much or as little as he wants about his current activity or purpose.
"That's a really interesting [shirt/watch/tattoo]. Does it have a story behind it?"
A specific compliment with an open-ended question encourages him to tell a personal anecdote, deepening the conversation.