I wonder if any of you have successfully converted a gal you met in RL to an SB (escorts and strippers don't count!).
It would seem fairly straightforward to ask a girl out on a date but somewhere along the way you have to get across that you don't want a traditional dating relationship. Interested to see if and how you guys have managed this.

But of course, too awkward if she says no.

What?  You mean there are girls in real life you can meet?  Who knew! (LOL)

...until you said strippers and escorts don't count!    

 
Accomplishing this requires a bit of circular logic.  You can't offer to be her SD if she doesn't consider herself an SB. And if she considers herself and SB she's (probably) already using a Sugar Site. Although I have met a few SB's who told me of an early/first Sugar relationship where a "rich guy" or a "rich couple" offered her something...  

 
Consider the likely process:  

 
You meet a nice girl - somewhere. Maybe a party, at the grocery store, your Uber driver, and of course, a bar.  

 
You start to chat and she seems both interesting and attractive.  

 
Along the way she drops some hints about being broke, being single, and maybe even jokes about wanting a Sugar Daddy and you think "Jackpot."  

 
But here's the problem: Is she serious? How does she really feel about P4P? If you go ahead and ask her about sugaring right away you risk 1-offending her by essentially calling her a hooker, 2-Getting slapped or kicked in the balls and then tossed out by the bouncer/host, etc., 3-Getting rejected because even if she would consider P4P for her she would never consider actually fucking you, or 4. She shows interest but does not realize that a SD does not equal a Simp.  

 
In other words, unless she already is or has been a SB, it's a risk to ask. And if she already is an SB, then she's not a "civilian" and so does not qualify for your question.  

 
What I have done in the past if/when sugaring comes up in a conversation, including when I brought it up (somewhat jokingly) when I saw an opening:  I ask her if she's ever really thought about it seriously.  If she says yes, I will ask a few more questions like: "Do you have any friends who have a SD?" Or "Have you ever tried to meet someone for that?"  

 
If she's "leaning into" these questions (so to speak), then it's time to start the sales process by generating interest.  "Let's talk some more about this soon. I'll give you my cell and I invite you text me if you are interested..."  

 
Then leave the conversation. Either go talk to someone else or change the subject or actually leave the area.  You just want to intrigue her and let her know it could happen. Then let her sell herself on the idea and contact you when she's ready to have a serious conversation.  

 
BTW:  This have NEVER worked for me.  

 
The closest I ever came (no pun intended) was a girl I met at a popular bar (think Yard House, but a different company) when grabbing a beer with a buddy (who knows I Sugar). She sat near us - 1 open stool between - at the bar and asked the bartender to recommend a glass of wine. I am an Oenophile (translation: Wine Snob) and jumped in to ask her questions about what she liked in a wine and then suggest a few options. That opened our chat, and she seemed a bit flirty and chatty.  Blah, blah, blah and after her 2nd glass she mentioned that her Uber bill was killing her, and she really needed a car.  Blah, blah, blah, after her 3rd glass she mentioned that she just broke up with some douchebag and he was helping her with her rent. And there was my opening: I joked she needed a temporary Sugar Daddy until she got a new boyfriend. She laughed, but I could see some contemplation in her eyes...  

 
Eventually she told me she was leaving (heading home to pack for Vegas) but invited me to follow her on FB. I told her before she left that I'd be interested in that temporary gig if she was.... and asked her to DM me on FB.  She seemed interested and reacted positively, but she never followed up.  

 
Life is good

 
The Cat

Yes, once, and she's incredible; my favorite by far.  I'm going to try to hang on to her for as long as I possibly can.  I'm at the point now where I only see other girls to make sure she never smells the "has no other options" scent on me.  Seeing other girls actually feels like work at this point; that's how good she is.

As much as I'd like to claim bragging rights for "turning her" to the dark side: in hindsight it was mostly dumb luck.  I am no Lothario, that's for sure!

Here's what I can suggest, extrapolating from a sample size of one.

[ul]
[li] [b]Age gap helps.[/b]  Sugaring may not be widely accepted by mainstream culture, but the idea that older-guy-younger-woman age gap dating usually involves financial support is something that pretty much all adults are aware of.  If you only approach significantly-younger women the pool of ladies you get indicators of interest from might be small, but it is going to have a very high concentration of SB-curious women.

[li] [b]Location helps.[/b]  This seems to be much more acceptable in Scottsdale -- at least, you're less likely to get kicked in the balls.  I'm told Miami like this too (but even more).

[li] You're going to have to [b]consciously disable a bunch of your anti-ripoff defenses.[/b]  Pay for platonic dates (never more than three, and usually less).  Pay up front the moment you meet her.  Do all the things you should [b]never[/b] do when meeting girls on sugaring sites (which you aren't using for this), except sending money to people you haven't met in person (you should still never ever do that).  Accept the fact that you'll get ripped off a bunch of times for small amounts.  Treat it as the cost of doing business.

[li] It helps if you [b]meet her through some mechanism that involves paying her for something other than sex.[/b]  This gets the awkwardness of you handing her cash out of the way, because you get to do it once in a scenario that is very obviously not P4P.

Before "escort" meant "woman who has sex for money" it had a more reputable meaning -- a gorgeous young lady who would sit next to a single guy at the theater so he wouldn't look like a loser.  These sorts of things still exist, and I use one for exactly this purpose, but you have to look for them and vet them carefully to make sure they aren't just a cover for sex work.  No, I won't say which one I used.  I will say that I met six ladies through this mechanism and only slept with two, and I'm completely okay with that because I expected zero.

Since you're both already comfortable with you handing her money for non-sex reasons, that's a good time to drop some hints -- but you have to be very careful: escalate first, make sure she's interested and attracted.  I recommend waiting until the second date or later before even hinting at this.

[li] [b]You're going to have to have some Game.[/b]  You have to be attractive in some way.  I'm short and not particularly handsome, but I work out like a fiend and am in much better shape than most people a decade my junior.  This is high-maintenance.  It's a lot more than a hobby, it's like a part-time job.  It's also expensive.  Dress well, drive a flashy car; it sounds cliche but these things actually work.  And you'll have to keep doing these things in order to keep her, so get used to them.

[li] [b]She has to be at least somewhat attracted to you.[/b]  This isn't like ordinary providers, where the bar is "not grossed out by the guy".  The bar is higher here.  See previous point.

[li] When you sense that intimacy is possible, [b]take her to your home, not a hotel[/b].  She'll feel a lot less like a sex worker.  Your place needs to be impressive (see previous point); consider renting a luxury condo for a year.

Weird hack that I stumbled into by accident: [b]show her your closet[/b].  She will immediately look for women's clothing.  This is one of those "how to find out if he's cheating on somebody with you" tips women's magazines teach young ladies, so let her use it!  It's the easiest way to demonstrate that you're single (well, that plus not having a tan-line on your left ring finger).  If you're not single then honestly you have no business doing this; discretion comes from experience and these civvie girls by definition have none of that.
[/ul]

PS, where is the TER forum formatting "cheat sheet"?

This is a great question; I will definitely use it!

I enjoyed reading your "how to" but disagree with that last statement.  I'm very happily married, in a very open, poly ENM relationship with my awesome wife.  All my playmates, and hers as well, have understood and respected the primacy of our marriage.  If I was chatting up a civvie, she'd be informed from the start about my marriage.  And if she was still interested, we'd take things forward from there.

Ah you're right!  Mea culpa, I totally overlooked this possibility.

I should have written "if you're cheating on somebody then you have no business doing this".