Most of my early conversations went absolutely nowhere. We'd text for a week or two and then just... fizzle out. No meeting. No arrangement. Just wasted time.
Then I figured out there's actually a rhythm to conversations that lead to actual meetings vs conversations that die out.
This isn't a clean step-by-step process. It's messy. But here's roughly what works.
The biggest mistake I made
I treated these like regular dating app conversations. Meaning: endless small talk, getting to know each other, building rapport for weeks before suggesting we meet.
This doesn't work for sugar dating.
Regular dating: You have time to build tension and connection over weeks of messaging.
Sugar dating: If you're not meeting within 10-14 days, it's probably not gonna happen.
The guys who are serious want to meet relatively quickly. The guys who text for months without meeting are either time wasters or stuck in fantasy land.
I learned this after having maybe 5-6 conversations that went on for 3-4 weeks and led nowhere. Complete waste of time.
The timeline that actually works
From first message to first date: 7-14 days
Breakdown:
- Messages 1-3: Building initial connection (days 1-3)
- Messages 4-7: Discussing expectations (days 4-7)
- Message 8-10: Suggesting video call (days 7-10)
- Video call: Usually within a week of suggesting it
- First date: Within a week of video call
Total: 10-14 days from first message to sitting across from them at a coffee shop.
Sometimes faster (I've done 5 days), sometimes slower (I've taken 3 weeks for people I was unsure about). But generally 10-14 days is the sweet spot.
Messages 1-3: The connection phase
What's happening: Figuring out if you can have a normal conversation.
What you're NOT doing yet: Discussing allowance, expectations, arrangement details.
What you ARE doing: Normal getting-to-know-you stuff. Their work, your school/work, hobbies, interests, basic personality.
Example exchange that worked:
Me: "Hey Marcus! I saw you work in real estate development - I'm fascinated by how cities evolve. What's the most frustrating part of getting projects approved?"
Him: "Ha! Zoning regulations are a nightmare. It's like navigating a maze. What draws you to urban development?"
Me: "I'm finishing my architecture degree - basically why I'm obsessed with how cities work. When I'm not drowning in studio projects I'm probably at coffee shops sketching buildings. What made you get into real estate?"
Him: "Started with property flipping after college and got hooked. The problem-solving aspect is addictive. What kind of architecture are you focused on?"
Me: "Mostly residential and mixed-use. I love creating spaces where people actually want to spend time. Your projects sound way more complex than what I'm working on. How do you deal with all the red tape?"
This is just... conversation. No mention of arrangements yet. Just seeing if we can talk like normal humans.
By message 3-4 you should have a feel for:
- Can they hold a conversation?
- Do they seem like a real person?
- Is there any chemistry/compatibility?
- Are there obvious red flags?
If any of these are no, don't continue. Move on.
Messages 4-6: The transition to reality
This is where most people mess up. They either:
- Stay in small talk mode forever
- Awkwardly jump straight to "so what's your allowance"
Both are wrong.
What works: Natural transition acknowledging why you're both on this platform.
Example that worked for me:
Him: [Responding to something about my school situation] "Architecture programs are intense. Are you working while in school?"
Me: "Part-time at a design agency but honestly it doesn't pay much. Which is why I'm here being transparent - I'm looking for financial support while finishing my degree. Hoping to find someone established who values mentorship alongside companionship. Is that aligned with what you're looking for?"
Notice:
- I acknowledged my financial situation (honest)
- But framed it as "support while finishing degree" not "I'm broke and desperate"
- Made it clear what kind of arrangement I want
- Asked if he's aligned
His response told me everything I needed:
Him: "Yeah that makes sense. I'm looking for something consistent with someone intelligent and genuine. What does your ideal arrangement look like?"
Green light. We're on the same page. If he'd said "let's just see where things go naturally" or "I prefer to discuss that in person" - red flags.
Messages 6-8: The expectations conversation
This is where you get specific. What I learned: Don't dance around this.
Bad approach: "I'm flexible, what do you usually do?" Good approach: "I'm hoping for monthly allowance around $X with 2-3 meets per month."
You can be open to negotiation while still setting an anchor.
Example exchange:
Me: "I typically prefer monthly allowance arrangements - I find they work better for building something consistent. Usually looking at 2-3 meets per month. What structure works best for you?"
Him: "I usually do monthly as well. I travel a fair amount so flexibility on scheduling helps. What range were you thinking?"
Me: "Based on my research and what seems standard in Chicago, I'm thinking $3000-3500/month. Obviously open to discussing what makes sense for both of us. What's your typical range?"
Him: "That works for me. I'm usually in the $3000-4000 range depending on frequency and connection."
Boom. We're aligned. If there's huge mismatch here, better to know now than after meeting.
Messages 8-10: The video call suggestion
By this point you should know:
- You can have conversations
- You want similar arrangements
- Allowance range is aligned
- Logistics work (location, availability)
Time to suggest video call.
How I phrase it:
"I feel like we're pretty aligned on what we're looking for. Want to hop on a quick video call sometime this week? 15-20 minutes, just to make sure we have good chemistry and confirm we're both real people. I'm free [specific day/time] or [specific day/time]."
Why this works:
- Summarizes where we are (aligned)
- Suggests next step (video call)
- Gives rationale (chemistry + verify realness)
- Offers specific times (makes it easy to say yes)
- Keeps it low pressure (15-20 minutes, no big commitment)
If they dodge the video call suggestion, that's a red flag. Serious people do video calls. Scammers and catfishes avoid them.
The video call
I don't love video calls but they're necessary. Weeds out catfishes, scammers, and people you have zero chemistry with.
What I cover in 15-20 minutes:
- 2 minutes: Small talk, getting comfortable
- 5 minutes: Confirm arrangement expectations one more time
- 10 minutes: Natural conversation to check chemistry
- 3 minutes: Suggest meeting if it went well
Example closing:
"This has been great! I feel like we have good energy. Want to meet for coffee sometime this week? I'm free Thursday afternoon or Saturday morning."
If video call went badly, I'm honest:
"Thanks for chatting! I'm gonna think about next steps and get back to you."
Translation: Not interested but being polite about it.
Setting up the first meet
After a good video call, suggest meeting within a week. Longer than that and momentum dies.
Where to meet:
- Coffee shop (my go-to)
- Casual restaurant for lunch/early dinner
- Wine bar
Don't suggest: Their place, your place, hotels, anywhere private.
When to meet:
- Daytime or early evening preferred
- Weekday afternoons are great (public, not too late)
- Weekend brunch/lunch works too
How long:
- Plan for 1-2 hours
- First meet is usually unpaid (mutual screening)
- If it goes well, discuss starting the arrangement at second meet
Common ways conversations die (and how to avoid them)
Problem: Texting for weeks without progressing. Fix: Move to video call by day 7-10 max.
Problem: Guy wants to meet immediately (same day/next day). Fix: Suggest video call first, then schedule meet for a few days out.
Problem: Guy avoids video call, wants to meet in person first. Fix: Insist on video call. If he refuses, move on. Probably a scammer.
Problem: Conversation is going well but neither person suggests next steps. Fix: You take initiative. Suggest video call around message 8-10.
Problem: He wants to discuss everything "in person" including allowance. Fix: Discuss basics before meeting. Saves everyone time if you're not aligned.
Problem: You're talking to 10 people and can't keep track. Fix: Focus on 3-5 top conversations. Let others fizzle.
Red flags that showed up in conversations
Won't video call: Almost always a catfish or scammer.
Pushes for in-person meeting super fast: Either impatient or not serious.
Wants to send money before meeting: 100% scam.
Asks for photos/videos before meeting: Sketchy. Decline.
Story doesn't add up: Details change, timeline is inconsistent. Lying about something.
Overly sexual early on: Looking for escort not sugar baby.
"Let's see where it goes naturally": Translation: wants free dating.
Won't discuss expectations: Either broke or time waster.
All of these I learned from experience (aka getting burned).
My conversation management strategy
At any given time I try to have 3-5 active conversations.
Why not more? Can't keep track. Names get confused. Energy gets spread thin.
Why not less? If one fizzles I don't have backups.
I keep notes. Yeah I'm that person. Name, key details from profile, where we are in conversation, when I last messaged. Helps me stay organized.
When a conversation is clearly going nowhere (they stop responding, won't progress, red flags), I stop investing energy. Don't formally end it, just... stop prioritizing it.
Focus energy on the 1-2 conversations that seem most promising.
Things I wish I knew earlier
You don't need perfect chemistry to meet. I used to only meet people I felt amazing about. That's too selective. Meet anyone who seems decent and aligned. Chemistry feels different in person anyway.
Video calls tell you way more than messages. I avoided them initially because awkward. But they save so much time. If video call is bad, you just saved yourself from a wasted first date.
The guys who are serious move fast. If someone's hedging about meeting, they're probably not serious.
Most conversations will go nowhere. That's normal. Don't get attached before meeting.
Moving to text/phone number should happen after video call. Not before. Keeps things professional until you know they're serious.
First meet is screening, not the arrangement. Don't expect payment for first coffee meet. It's mutual screening.
My success rate
Out of every 10 first messages I send:
- 4 people respond
- 2-3 lead to actual conversations
- 1 leads to video call
- Maybe 1 out of every 2-3 video calls leads to first date
- Maybe 1 out of every 2 first dates leads to arrangement
So roughly: 10 messages → 1 arrangement.
This means to find 2-3 good arrangements, I need to message like 30-40 people. Factor that into your timeline.
Timeline reality check
Fast track: 7 days from first message to first date (rare) Normal: 10-14 days Slow: 21 days Too slow: 30+ days (probably won't happen at this point)
If you're past 3 weeks of messaging without meeting, something's wrong. Either they're not serious or you're not pushing things forward.
The uncomfortable parts
You'll probably lose interest mid-conversation: This happens. Someone seems great in their profile but the conversation is boring. It's okay to let it fizzle.
They'll lose interest mid-conversation: Also happens constantly. Don't take it personally. They met someone else or changed their mind or who knows.
Video calls are awkward: Especially first few times. Gets easier with practice.
First meets often have no chemistry: This is why you go on multiple first dates. Most won't lead anywhere.
You'll ghost or be ghosted: It's rude but it happens. Try not to but also don't stress when it happens to you.
What works for me might not work for you
My conversation style: Direct, efficient, move things forward quickly.
Some people prefer: More rapport building, slower progression, more emotional connection before meeting.
Neither is wrong. But know your style and adapt accordingly.
If you're naturally more reserved, maybe take 3 weeks instead of 10 days. If you're naturally direct, maybe 7 days is fine.
The key is moving things forward intentionally, not letting conversations drift forever.
Final thoughts
Sugar dating conversations are different from regular dating conversations. They need to progress faster. They need to cover expectations explicitly. They need to lead to meetings quickly.
Most people either move too slow (weeks of texting) or too fast (meet same day with no screening).
The sweet spot: 10-14 days from first message to first date, with video call in between.
Figure out what works for you and iterate on it.
Anyway that's basically everything I've learned about the conversation phase after doing this for 2+ years. Your experience will probably be different but hopefully this helps.
Now go message some people and actually suggest video calls when it makes sense.