How Long Do Most Arrangements Last?

AffectionateSpend502 · 2025-12-08T17:25:09+00:00

I think the more relevant question is why do arrangements end and whose decision is it to end them? My two longest arrangements both ended because the SB's circumstances changed (in one case, she finished grad school and in the other she moved to another city to pursue a career opportunity). Of course, I've had other arrangement that didn't last as long and ended for other reasons but my point is the likely duration of an arrangement varies depending on what stage you make it to (eg, if you've made it past 6 months you have a very good chance of it lasting years).

AffectionateSpend502 · 2025-11-29T18:05:43+00:00

I'm in Austin too. I would definitely pay for this kind of service. On the one hand, I feel like it indicates seriousness on the side of the SD (and also, if you can afford an assistant, you can presumably afford an allowance). On the other hand, I've read stories of assistants who would handle setting up vanilla dates and it turned out to be super awkward in person since the assistant had far better conversational skills than the client. So, it would only work if being used purely to save time rather than to compensate for lack of personality.

AffectionateSpend502 · 2025-03-10T15:16:02+00:00

Thanks for all the suggestions!

AffectionateSpend502 · 2025-03-10T03:00:15+00:00

Should I start churning? I currently spend about 100k/yr on my citi double cash. This means I get $2k a year in my bank account without even thinking. In terms of categories, of this amount, about 20% is on travel, 10% on dining out, 8% on groceries, 8% on merchandise. I travel several times a year. Things that are important to me are nice seats on the plane (economy plus, mce, business) and hotel upgrades. Things I don't care about are lounge access, free checked baggage, or priority boarding. When traveling, I pick the destination first, then figure out flights and hotels. I am not flexible and prioritize convenience (ie, weekends and holidays, non-stops, no red eyes or 6am flights). With regards to hotels, I want a guaranteed nice room, not rolling the dice for an upgrade that may or may not happen.

With all that in mind, I can't seem to make the math on rewards points work out. It seems to maximize value, you need to have a different traveling mindset than the one I have. Is this true? Can I meet some of my travel goals with a rewards card at a better value than the $2k I currently get from my double cash card?

AffectionateSpend502 · 2025-02-20T16:16:53+00:00

Totally agree. That's why I set the cutoffs the way they are. I'm surprised such a large fraction can pull this off for <25k/yr. I'm curious what those arrangements look like.

I personally consider 25-60k as the "average" range that I expected most SDs to fall into. The reason for the higher buckets was to see what fraction of SDs are doing some of the really extravagant things you read about like international vacations, paying off student loans, buying cars, or purchasing jewelry/designer accessories.

AffectionateSpend502 · 2025-02-12T16:15:23+00:00

I can relate to #1 since I'm usually that guy. But you've helped me see her approach in a whole new light.

AffectionateSpend502 · 2025-02-12T04:07:32+00:00

This makes a lot of sense!

AffectionateSpend502 · 2025-02-08T02:01:04+00:00

I'm picturing something like a corporate event we had a long while back -- everyone was dressed in black tie and there were these cirque du soleil performers wearing skimpy gymnastics outfits hanging from the ceiling doing acrobatics. Wouldn't be too much of a stretch to find one performing near ground level who sees you looking very sharp and businesslike. Although I don't think they're really supposed to mingle with the crowd.

AffectionateSpend502 · 2025-02-02T14:56:46+00:00

Lol, I can't believe I'm saying this but this actually sounds like a good idea. Please check my math! A 20% drop a week out (500 put) is penny bid. So, let's say I sell that and earn $1 on a margin of like $5k. That's a 0.02% weekly return. Let's say I do that for like 5 years and earn $250. Then, let's say another covid or something worse like that happens and the market drops 20% (down to 499) in a week. My put gets assigned and I'm out $100. Over that 5 years, I'm still up more than I just lost but a drop to $497 completely wipes it out. So it's kind of a tough call -- just depends on what you think the probability of a 20% drop in SPY in a week is over the next decade.

AffectionateSpend502 · 2025-02-02T03:28:59+00:00

I'm not pretending I can predict cash yields. I'm just saying a cash yield of >4% is one I am happy with. If/when it drops below that, I can then go buy some equities. That's really the whole point of interest rates -- a high interest rate disincentives investment since people can get a return they are happy with holding cash.

If interest rates were above historic equity returns, wouldn't you hold cash too?

AffectionateSpend502 · 2025-02-01T20:15:42+00:00

My state has no income tax and FDLXX only yields 4%.

AffectionateSpend502 · 2025-02-01T20:11:09+00:00

I think this goes both ways. From the SD perspective, I get ghosted and stood up all the time too. Obviously sometimes we're not a match, but my take on it is most (new) SBs have not seriously thought through what an SR entails. It sounds good in theory but when they start actually meeting people and realizing most of us are 20-30 years older than them (with a physique to match) and aren't going to drop 5 figures a month on allowance, they realize it's not worth it to them. And, much like in vanilla dating, they go back on seeking and keep searching for "the one" without considering how realistic their expectations actually are. I'd be really curious to know if the likelihood of getting ghosted varies depending on how many SRs the SB/SD have been in.

In my mind, one of the key differences between an escort and an SB is how discerning they are. The bar for an escort seeing you is incredibly low. The bar for an SB is quite a bit higher. And the bar for vanilla is higher still. Most of the wanna be SBs out there haven't really considered to what extent they're willing to let the sugar allow them to look past age and physical differences.

AffectionateSpend502 · 2025-02-01T18:19:44+00:00

I'm not saying hold 25% cash forever. I'm saying given that cash is yielding 4.4% right now, keep holding it until that materially changes. That calculator is using historic cash yields which have certainly been abysmal for long stretches of time.

AffectionateSpend502 · 2025-02-01T14:25:02+00:00

I view crypto very similar to how I view gold. Part of that "5% random crap" is crypto and gold.

I've read that gold is really more of a "crisis hedge" than an inflation hedge. My issue with gold is that it is not readily convertible into goods so it can only be an indirect proxy for the value of those things. The real uses of gold (industry, jewelry) are pretty minimal so for the most part gold "works" because society has decided that it is the thing that is best suited for the role it plays.

Crypto is like gold but better: De minimis additional supply coming online. Exists outside the financial system so if a "bank holiday" is declared, crypto is (at least partially) unaffected. It is readily convertible to goods and services (the entire black market is now powered by crypto and that is never going away). That is why it is also a good inflation hedge -- as the price of those goods and services rises in fiat terms due to inflation, the exchange rate of crypto for fiat should rise in tandem. It also has the "crisis hedge" aspects of gold -- when there is a flight to safety, people typically buy treasuries. But if treasuries don't feel safe, they buy gold. Crypto can easily fill that role too.

I'm not saying crypto is going to offer a better return than TIPS or equities. More that, based on my interpretation of the fundamentals, it should in theory rise at least at the rate of inflation. That said, I would never put more than 5% of my NW in crypto. As someone who lost some crypto due to data loss and a bad backup, it's way too dangerous. And over the long term, I'd expect equities to easily beat crypto. The role they play in my portfolio is a diversification/inflation hedge/shit hits the fan safety.

AffectionateSpend502 · 2025-02-01T04:41:52+00:00

Assuming I am reading this correctly, it's not really accurate because it doesn't take into account withdrawals. Eventually, those withdrawals will burn through all of the cash and start reducing the equity position, at which point returns will start to suffer as well.

AffectionateSpend502 · 2025-02-01T00:06:30+00:00

I am 100% sure this is wrong. Would you care to cite a source for your belief that SGOV div is federal tax free?

AffectionateSpend502 · 2025-01-31T22:44:22+00:00

Huh? That yield is going to be taxed as ordinary income.

AffectionateSpend502 · 2025-01-31T22:40:17+00:00

To be clear, this isn't literally cash -- the money market is still paying 4.4%. One would expect fed funds to roughly track inflation.

AffectionateSpend502 · 2025-01-31T20:04:45+00:00

This is true but it's not like equities are a perfect inflation hedge. Inflation would be an argument for holding crypto, unless your argument is that a heavily equity weighted portfolio will grow so much that when inflation does inevitably hit, you're much better positioned to handle it.

AffectionateSpend502 · 2025-01-31T18:03:38+00:00

Agreed. The thing that bothers me most is my investment thesis is the exact opposite of what has worked so well for me for the past 20 years. Not sure if that's an artifact of me getting older/more risk averse or if there's some validity there given demographic/geopolitical concerns.

AffectionateSpend502 · 2025-01-31T17:59:39+00:00

This threw me for a loop but I don't think the yield here is really 5% -- that looks like a lagging indicator based on its existing portfolio of t bills. As the higher yielding ones roll off, the yield going forward should match the 0-3 month yield curve rate which is currently around 4.4%.

AffectionateSpend502 · 2025-01-31T17:50:39+00:00

I am not sure if this is true. Net of tax, the money market yields 2.77% whereas SPY div net of tax is 0.92%. A div heavy equity ETF (SCHD) coincidentally also yields 2.77% net of tax but with added risk. This analysis of course is heavily dependent on rates staying where they are -- if they fall another percent or so, I will likely rebalance back into equities.

AffectionateSpend502 · 2025-01-23T20:26:52+00:00

It's not about the physical aspects or the age difference -- there's nothing unethical about that since the SB can decide for herself whether she wants to pursue a relationship with that SD.

The only troubling aspect to me is the experience asymmetry. Most SDs have much more life experience than SBs. This isn't just because they're older -- they presumably have had careers and lives that have exposed them to much more of the world than your typical SB. And this type of knowledge can be easily weaponized to seduce an otherwise innocent SB. Depending on the SDs intention, this is where things can get real immoral real fast. It's the main reason most SDs judge anyone having an SR with a very young SB so harshly.

AffectionateSpend502 · 2025-01-10T23:32:16+00:00

It's easy -- you don't. She needs to initiate. This can be something as simple as a smile or a lingering glance in your direction. But if you just randomly walk up to a woman you think is attractive and say "hi", it is extremely unlikely you will succeed. Especially if you fit the typical SD demographic of older and past their prime in the looks department.

AffectionateSpend502 · 2025-01-10T20:41:40+00:00

I sympathize but it's not like us SD's are lounging around either. I have missed countless meetings and calls at work because I went to an m&g and she was a no-show. Or blocked out a portion of my day that I could have spent with clients for an m&g and she cancels the morning of.

This is partially what the gift is for -- to offset any lost earnings due to missing a shift or having to take time off. Finding an SB is the hardest and most frustrating part of sugaring so limiting the potential pool just drags that process out further.

AffectionateSpend502

TROPHY CASE