So I met a POT about 2 years ago for a M&G.  Young, blond and pretty and we seemed to get along well.  We met again a few days later with her friend (safety net?), young, black, pretty and sort of a hybrid "goth-LA Street" style,  and we all had dinner - just dinner. A few days after that, the POT flew home to Canada and I wrote it off. But I kept in touch by Twitter with her friend (who lives local to me), even though the friend showed no interest in sugaring.  
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Skip forward to last week. The friend reached out to me through a Twitter DM and half-jokingly asked me to get her a pizza. I had Pizza Hut deliver and asked her if she wanted to visit me so we can cath up. She agreed. The first scheduled date was a last minute cancel when she said she had to help her father with an urgent problem.  I assumed it would never happen so I wrote off the $23 for the pizza and prepared to move on. But she followed up and asked to rechedule the following week, if I could Uber her to my place (about $45). I agreed and suggested dinner at a nearby restaraunt.  
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She arrived on schedule and we went off to dinner. Since I had origianlly met her, she has quit recreational drugs including weed (which is now fully leagal here) and alcohol. In addtion, she is looking for a "real" job as her alt modeling gigs (they were legit - I saw the published pics in alt magazines) were spotty and she is just starting to develop a music career (by self producing, publishing and distributing) and wants to get stable income to let her focus on creating music. During the meal she mentioned that she was aware her (now former) friend met me through a sugaring site. So I aksed her if she was interested in trying that lifestyle with someome. She said she didn't mind the idea. We left it there since we were in a public location. But when I took her back to my place we kept chatting for a while. I deliberately did not bring up the topic agian. Didn't want to appear pushy or too anxious. Of course, about 45 minutes later, she did - sort of. She mentioned that she would like to know more; how it worked, what was expected, etc. She did not specifically ask me about an arrangement with me, and I kept it all 3rd party for a while.  Again, soft sell seemed the way to go.  
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It was getting late, and she needed to head home soon. I finally asked her if she was interested in exploring an arrangement with me. She said she was but wanetd time to think about it. We talked a bit more specifically about my last arrangement (note: I always describe other arrangements in the past tense) and I described a casual format (2 to 3 times a month for a meal, some activity like a movie, drive, or shopping and some time at my place). I did not mention any allowance numbers. Just hinted that I'd give her a gift to help her with bills every time I see her. Off she went and we stayed in touch (by pizza delivery) over the next week.  
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Three days ago I aked her if she has been thinking about our discussion. She has and wants to try it.  Of course I agreed. I left it alone for a full day. Then last night I sent her a message asking if she wants to try "staying overnight" with me sometime soon.  She does. Then I asked her if giving her xxx allowance when I see her would help her. She said it would.  No push back or negotiation. I'm pretty sure this is completely new to her. In me she finds a mature, nice guy who respects her, expresses genuine interest in her and who she trusts.  While I think her past experiences with dating men are almost certainly limited to guys her age (21) who have been typically misogynistic, self-centered, and poor.  
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I let her pick a date this week (or next if she's "not ready yet") and she picked a date early next week. So I'll still need to cover an Uber to and from, plus some dinner (DoorDash).  
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The lesson here:  Never burn bridges. Always stay open to communication and maintain a friendly, casual relationship. (Unless she proves to be a bad actor, of course). Developing this opportunity occurred over a 2 year period. Don't know if that's a record, but the reality is it look little effort and the cost of 3 pizzas to get to an arrangement. I will report back once the meeting date occurs. She may not show, she may reschedule then not show, she may just ghost me. Or she may rock my world.  
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Life is good.

about never burning bridges.

However, you haven't quite crossed this bridge yet.

Be sure to let us know how this story turns out.

-- Modified on 4/30/2018 1:17:33 PM

Two years is the longest period so far that I have exchanged messages with a potential SB on SA, on and off, whenever she logged in which was rarely.  I never berated her for failing to answer my messages, always told her how glad I was to see her active again, etc.  After two years she finally decided to meet me and we've been Sugar Dating for over a year now.  Gorgeous luscious 22yo blonde.  So yeah, never burn bridges, always keep those options open, because you really never know!

but I do have a question. If she was the one who brought up "sugaring" AND if she was comfortable enough to come to your house and continue the discussion about it, why didn't you at least run up a trial balloon about her real interest by trying for a kiss, hold hands, or in some other way get to take a read on her body language to see if she might have been ready to hop into bed with you right then?

 
So far while I have not actually had sex with every single POT SB that I have brought home with me on that first date, my average is well over 90% and of the couple of times where we didn't have sex we at least made out a bit. It's been my experience that virtually all women that will go out on a date with you, have open conversations about sex, and then agree to come to your home are at least "interested" and while not all of them will actually have sex with you on that first date, it's pretty much a given that at least "something" physical is going to happen between us.

 
Ironically, speaking of pizza, I broke one of my usual rules with my last POT SB. We had been talking by text for a few days before having our first actual date, she had been ready to meet, but it was my schedule that prevented it, this was a little over a week ago. That Friday was her birthday and since I couldn't get free to see her she went out with friends and overdid it a bit, during our conversation the next day she mentioned just like your girl in a "half joking" kind of way that she could use a pizza to cure her hangover, so ironically enough I bought her a Pizza Hut pizza too and had it delivered to her home.  I know this technically broke my own rule about giving a single penny before meeting, but I really couldn't see the harm in treating her to simply pizza. The story has a happy ending, we met for dinner a few nights later, had a nice little make out session in the parking lot after dinner and she came over and fucked my brains out the day after that. I think she is going to be a very welcome addition to my "rotation" lol

Fair question, GaGa. I shall address it below...
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Q: If she brought it up, why didn't I try to make out?  
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Short version: I felt that was too agressive given the context.  
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Context: As far as I can tell she has been living her entire sexual life (perhaps as brief as 2 to 3 years?) through hook ups and short-term BF's who ultimately disappointed or outright disrespected her. She has a farily large social media (Twitter and IG) presence with over 26k followrs. In that space, she comes off as brash, hard core "fuck the world if you don't worship me" and "LA Street Hip".  But face to face, with just a nice regualr guy who's not the slightest impressed by that, she comes off as a young, shy, introverted woman trying to find her way in a big world with little familty or friend support. It just didn't make sense to me to push any physical agenda too soon. I don't know that she contacted me with the hope of pursuing sugar, or if she just wanted to play an old white guy for a free pizza. But she found a person who treated her like she matters in the world and who didn't judge (in fact admired) her style, point of view,  and dreams, even though I obviously roll in a different direction. So when I invited her to come visit me - and just visit me - she may have slowly rethought about the potential of a deeper relationship with me. I appeared to have no immediate agenda other than friendship and support. It just seems more holistic to let her broach the sugar concept, or at least hint that she wanted to know more.  
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Note that we did have a fairly specific discussion about what a sexual relationship could look like, including my insistence on mutual testing and my preference for delivering and prioritizing her pleasure before mine.  Also, with a 2 year journey to this point, rushing or pushing to "get a win" seemed counterintuitive. I guess it's a "let her chase me until I catch her" strategy.  
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As to the "pizza as method to start a conversation" topic: I looked at it as generally less-than or equivalent to the funds/time I would invest in a new M&G without BCD.  Honestly it was a low-percentage shot. I did not expect her to agree, let alone actually show up (after one canclellation!) to meet with me.  But she had previously been to my home with her friend and had experienced hang time with me. So I presume that past-experience helped her feel safe coming to see me. I don't imagine she would do that with someone she had not previouly met.  Finally, as far as I can tell she has not and will not create a profile on SA or any sugar or dating site.  So I am possibly the only example of a sugar daddy she knows, beyond perhaps some rapper-stripper thing she may have experienced through media or even personal knowledge of friends.  
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Side note:  I have a dinner date tomorrow night with a 22 year old AA stripper.  I met her about 10 days ago and I joked while getting a lapdance that she really needed a good sugar daddy and she perked up at the idea. Later she asked for my phone and has texted me once or twice a day since. I suggested dinner and she agreed with no ask for $$, suggestion of P4P BCD or even an enticement to see her again at the club.  She is absolutely smoking hot, tall (5'8") and rail thin, maybe 115 lbs with a models' face and long hair. Just my type, excpet she isn't Asian. LOL.  She's in college, plans on being a dentist and also works a day job... more updates to follow.

Herb, Sweet, and Gaga, i am always impressed and entertained by your stories. Wish i had your game and closing ability. Alas i suffer from being a wuss. Lol

I do get a few Subs now and then but my closing % is nothing like you guys.

and given the situation and lead up to where and how you ended up where you are/were with her I actually agree that you made the right decision. Putting it into "sales speak" there are a couple of schools of thought on the subject. One is ABC, (Always Be Closing) and while I have to concede that approach will yield a lot of "wins" it also makes that person a royal PITA and that kind of heavy handedness can also have the effect of chasing off prospects that need gentler handling.  I fully agree with you that "going for the close" is only warranted when the POT SB has given you enough signs, (body language, mutual touching, etc) that shows she is likely to be receptive to your "move" on her, and until she is ready any attempt to move too fast can not only be offputting, but can kill any chances of her ever "being ready" as you go from nice guy to "just another jerk" with just a single badly timed advance.

 
As for the pizza, I know it goes against everything I have ever said about "no sugar before BCD", but I am with you on this one too. Springing for a pizza is different than "sending" money to a POT SB, partly because you know WHERE the pizza is going. Having a local, or semi local address to have a pizza sent to is a lot different than using VENMO to send some scammer money, never to be heard from again, and to be honest if I were to get scammed out a pizza I am not going to feel even half as foolish as I would sending cash to a POT SB. It would have about the same impact on me as buying a drink for some chick at the bar that leads nowhere, I most likely wouldn't give it a second thought.

 
BTW my "pizza girl" texted me last night wanting to know when we can get together again. I hate to say this but my rotation is starting to get rather full. Besides the SBs I see on an infrequent basis,  I have two SB's that want to see me once or twice a week, another one who wants to meet several times a week, and now this girl who also has the potential to want to meet at least a couple of times a week. I may have to slow down cultivating new relationships until I lose a couple of the ones I am seeing now. Of course we all know how fast feast can turn to famine, so I don't think I will ever totally drop my efforts to meet new POT SB's

Thanks Rat, but I doubt my closing percentage is very high.  I'm just persistent as hell and keep working it all the time!