The above question is mostly for fellow hobbyists, but I welcome insights from providers too.

I decided to try being a sugar daddy as a happy medium between mongering and civilian dating. I signed up for a leading “arrangements” website and began communicating with sugar babies; I have been on eight dates. Below are some observations and lessons learned the hard way. I would appreciate any feedback or guidance on these issues and the general arrangements scene. I know “the rules of the road” for mongering and civilian dating, but arrangements are uncharted territory for me, so I would appreciate any pointers or rules of thumb. Above all, I want to know if you think that arrangements are better or worse than this hobby overall or in specific ways, and if you think that they are a viable alternative to or substitute for mongering.

I generally found the photos of sugar babies more attractive than those of providers. This observation may reflect my personal taste in body types, as it seems that a larger proportion of the sugar baby population is curvy or voluptuous. This observation may also reflect my preference for the more candid and realistic photos that many sugar babies use, rather than the professional and often edited glamor shots of many providers. Out of the eight girls that I met, all had accurate photos, and none of them disappointed me in person. Have you ever walked down the street, seen a hot girl, and said to yourself, “damn, I wish she were a provider!” That is the kind of girl that you find in the arrangements scene.  

Many sugar babies are effectively hookers. In fact, I saw photos of a well-reviewed provider on a sugar baby's profile, which otherwise matched the provider's description. Most sugar babies expect at least some token wining & dining before you fuck them, but others cut to the chase and either come to your place or invite you to theirs. One of my dates turned out to be an outcall to my apartment, even though I had offered to take her out to dinner first. Even sugar babies who claim to want a weekly or monthly “allowance” usually accept it on a “per meet” basis for each date in an initial trial period, until both parties are comfortable with a longer arrangement. I wonder how many of these “per meet” dates actually turn into longer arrangements, or if they differ little in substance from the “dinner date” packages that many professional providers offer.

If many sugar babies function in practice like hookers, then they are amateurs without reviews, and the quality of my experiences with them has varied wildly. I presume that the same is true for sugar daddies too – they would be like hobbyists without whitelistings or references. Compared to the hobby, the arrangement scene is the Wild West, with little or no way to vet your dates beyond talking to them, and no accountability – the only incentive for either party to behave properly (beyond basic decency) is the desire to avoid offending someone that you want to see again. Many of the sugar babies are extremely flaky, and it is difficult to get them to do basic things, like return calls and messages in a timely manner and show up on time, compared to the professionalism of most providers. All but two of the eight girls that I met were significantly late, and one of the two that arrived on time did so because I had arranged her transportation for her. I had arranged two other dates beyond the eight that actually occurred, but two of them stood me up without any communication – NCNS, in hobby terms. As for the quality of the sex, it was significantly lower than that of professional providers. Only one was top-notch, which I attribute to the combination of our greater chemistry and rapport and her origins in Latin America, where women generally fuck better. Another one was good, one was OK, one was mediocre, and three of them were abysmal; another had such an obnoxious personality that it outweighed her hotness, so I aborted the date after dinner.

A key advantage of the arrangements scene is its online and in-person “meet & greet” aspect, which is far more extensive than the occasional M & Gs in major cities for our hobby. In fact, it is an integral component of the scene. One interacts with other users of the website to assess compatibility and chemistry via some combination of reading profiles, exchanges of private messages and photos, phone communications, or in-person meetings (dinner, drinks, coffee, etc.) These exchanges can be very helpful to build rapport and identify those that may or may not be a good fit. I had a one hour phone call with the sugar baby with whom I have had the best date so far, which I took as a sign that we would be compatible, and it probably helped to build rapport for the subsequent date. This screening process is by no means perfect, however – I also had a substantial phone conversation with the sugar baby who was so obnoxious that I aborted the date, but I did not observe any indications thereof during that phone call; I suspect that she deliberately concealed her true personality in order to get the date.

The arrangements scene has much more YMMV than our hobby. Most hobbyists with enough money and screening details should have few or no problems booking a session with most providers, beyond age or ethnic restrictions (e.g. 40+ only, “no black guys,” etc.), unusually selective providers, and availability issues. You can reasonably expect to have a good time with a well-reviewed provider if you behave properly. Sugar babies are much more selective; many of them will not communicate with you at all if they see something that they do not like on your profile (e.g. photos, age, ethnicity, income, hobbies, goals for an arrangement, etc.), or they will abandon the conversation or date if they hear, read, or sense something that they do not like. The beneficial flip side of this YMMV is that you can have a much better time with the ones that genuinely find you appealing as something more than a source of income – as I believe to have been the case with my most successful date thus far. Sugar babies motivations' vary considerably – some have purely financial motivations, while others look for the same things that they would seek in a regular date, plus some money on the side.

Another dynamic that may be unfamiliar to hobbyists is the frequency with which sugar babies approach sugar daddies. I receive an average of 10-15 unsolicited messages from sugar babies each day. There are WAY more sugar babies than sugar daddies, so the competition forces the former to be proactive. Another lesson that I learned is to avoid any girl that makes the first move. Out of my eight dates so far, all of the ones that approached me turned out terrible, and all of the better ones were with girls that I had initially approached. This pattern best explains the varying quality of my experiences. My dates improved once I began ignoring unsolicited messages from new girls.

The other key factor is age. Three dates of my worst dates were also the oldest: 31, 30, and 27. The lower-quality experiences with the older sugar babies had nothing to do with appearance: in fact, the two oldest were also the two hottest. I believe that the older sugar babies focused more on what they wanted, both financially and physically, at my expense, which may explain why they initially approached me. I also noticed that older sugar babies tend to ask for more money. I had two mediocre dates and one bad date with 18 year-olds, whom I believe lacked the maturity and experience to have a fruitful arrangement with a man twice their age (I am 36). My best two dates (the only two that I will ask for a second date) were close in age to each other and a happy medium between the two extremes - 23 and 24: young enough to follow my lead, but old enough to connect with me in a meaningful way.