"Sugarbabies" / "Arrangements" Amateurs or Not?

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A2

[HollywoodGuy]

Could use some advice on this one.

Been chatting via text with a potential. She's probably about a 7 or 8. Interaction has been decent, nothing spectacular. I invite her to meet up this coming week and she replied back "I would love to meet up, however my twin sister will be coming with me. We are identical. It makes me nervous meeting people from online".

How should I play this?

Mmmm. Twins.

Never tried any two girl action off the SD site. But experienced mongers usually say its a bad idea. I won't meet any girl that wants to bring a friend. Not my thing anyway. But if its yours meet them at a starbucks. And don't go anywhere with both at the same time until you"ve banged at least one of them first..

[TacoLover23]

Could use some advice on this one.

Been chatting via text with a potential. She's probably about a 7 or 8. Interaction has been decent, nothing spectacular. I invite her to meet up this coming week and she replied back "I would love to meet up, however my twin sister will be coming with me. We are identical. It makes me nervous meeting people from online".

How should I play this?

Mmmm. Twins.

You have two plays here. Ditch it. You're going to get rolled. Or you're going to get rolled. Not worth it.

[TacoLover23]

Don't have a wife or SO. I use the SA App. It's cool. Let's you know who is close since you can search via GPS (the real GPS.) I have no problems with privacy since my work phone is separate and I keep those I don't trust on the work phone and my personal phone personal with very few contacts. I figure the company-issued phone only wants the dirt, so they don't care if I schedule a lunch with a close friend on it. My dirty friends have both #s. Of course, I don't have a SO, so YMMV.

Excited to meet my 3 POTS. Report will come soon when appropriate just because all of the awesome help on this thread. None of the POTs have discussed finances. So could all be GPS. Who knows? But like someone earlier said, welcome to the ride of your life? Yeah. Now I get it.

Anyway, anyone use the Burner app? I'm loving it. Forget SA app. The Burner app is where it's at.

[LandonR]

Could use some advice on this one.

Been chatting via text with a potential. She's probably about a 7 or 8. Interaction has been decent, nothing spectacular. I invite her to meet up this coming week and she replied back "I would love to meet up, however my twin sister will be coming with me. We are identical. It makes me nervous meeting people from online".

How should I play this?

Mmmm. Twins.

[IluvSmellyFish]

The approach you put out there is great. I've found that it also works with the younger girls who are more interested in experiences rather than just an allowance. While I have started to discuss allowance prior to the m&g, I've found that it has hurt me more than helped.

If you meet a girl and she would consider dating you outside of the site without the sugar, the sugar becomes a plus. On the other hand, if the sugar gets discussed up front and is too low, if you don't have a chance to show them that they would've gone home with you for free, then the talk of sugar kills things right off the bat.

Much more work. I know. Also this approach is worthless with girls that are only interested in the sugar and nothing else. The major downside though is with the younger girls, some may get it in their head that things will lead to more. I think grumpyinva has it right. A MILF will be more practical in her expectations.

I had to cut loose my redheaded sb1 because although she was a lot of fun, and a great an inexpensive baby to keep around, she wanted something that I wasn't able to give to her.

JeezLizard,

I liked your breakdown of the 150 k per year mentality. Stunningly accurate. Then they wonder why they're struggling, with so much "earnings potential".

I disagree on the MILFy perspective, though: I don't think the MILFs are intentionally there to build their egos or put the guys down. As someone who tends to prefer MILFs to the 20-somethings (although I've been making some exceptions to that this year. The 20-somethings are just MUCH easier to land,) the ones who are serious are VERY interested in keeping their SD happy, knowing that he has access to a good supply of 20-somethings who are hungry. The difference tends to come into when you make a $ offer to a MILF. If you're 21, and working at McDonalds, and someone offers you $1 or $1. 5, that's a really big deal. She just made 2-3 days of income, just for hanging out with a guy who's treating her better than her boyfriends have, plus she gets to feel the thrill of being "bad".

Once you're in your 40's, 2-3 days of income would still get their attention, but these are women who will normally be making upwards of 60 k per year, and $1 just isn't as exciting. They expect higher pricing for the same reason that you expect to get a higher salary each year in your job, even though that clearly doesn't apply to the market, here. If you throw out $ or $1. 5 into an early email, it's just not going to be that interesting to her, and she may reject you out of hand, even though it would be a fair representation of her market value in this arena.

On the other hand, girls who are 40+ do not expect to be going out with hot, washboard-abs surfer dudes, either. They won't be in the same condition as they were in their 20's, but you're exactly the kind of guy they would regularly date, anyway. If you have decent game, you can spin it as helping with a few things, while dating a very appreciative lady who makes herself available for you, while honoring your need for discretion. To be honest, it's not that easy to find affair-quality women who won't introduce drama at some point, but if you're in the $1. 5 range, and talk to the MILFs pretty much as you would if you were trying to pick them up on a regular dating site, by the time you're at dinner and they ask about your budget and expectations, $1. 5 will sound more like icing on the cake, plus they will not generally consider trying to replace your spouse or SO, because they have a more practical mindset, and they don't want the arrangement to end. Mind you, this only applies to the realistic ones, who realize that the very high rollers aren't going to be interested in MILFs, so their top expectation is a fairly regular guy who will be interested in them, appreciative of them, and who will add a little sugar to the mix.

So my best approach with them is to simply chat them up exactly as if you were on a regular dating site, politely defer any attempts to negotiation via email "I'd rather discuss specifics in person, after we see if we have chemistry," set up a date and make sure you've gotten their number, play a decent text-game with them with a once-a-day-at-most chatty little "Hey, how'd the _ work out today? BTW, I booked our table for Friday, so we could get the good one, by the window" stuff, and otherwise ignore them, until they try to engage you, then give them your full attention for the 10-30 min it takes her to tell you about her day. By the time you get to the date a few days later, they feel comfortable with you, and, again, you treat it exactly as a regular Match.com date, until they ask you about your experiences on the site, which is your cue to roll your eyes and complain about the hordes of 20-somethings that just don't have a clue what life is about, and then ask her about whether she's found any worthwhile guys so far. The MILFs tend to have less folks interested in them, and they're less approachable, so you have comparatively little competition for her attention, and she has already decided that you're someone she would probably date for free, so that's usually the point at which they are ready to be talked into setting up a second date. When they ask about expectations, you can comfortably float the $1. 5 "for when we reach that stage in the relationship," and then let her talk herself into accepting it, since she's not going to reject it out of hand at that point. MOST of the time, they'll quickly suggest that the second date could include some private time together, "if you're interested". Make sure the second date happens relatively soon (before they lose their nerve,) and you're in.

Okay, yes, that's a lot of "work", but it tends to result in a reliable MILFy SB who's fine at $1. 5 (even if she would've rejected that, up front,) and who won't have a second thought about starting early in the day, and staying overnight for that. One of the hardest parts, though, is finding one that you're attracted to, since the pool of MILFs is much smaller than the pool of younger SBs, but it's already a given that trying to groom a SB is harder than just wandering over to BP, with significantly more return, if things work out well.

And I still wish I had Hollywood's powers to keep a stable of attractive SBs at $1 each, but, for now, I'm on the much lower-numbers and slightly higher-cost list!

[HollywoodGuy]

All good advice here. I guess my desire for a hot MILF will have to be weighed against the ease of getting a young girl and the extra time needed to woo a MILF.

Oh woo is me. I got tired just reading about the approach. But it all makes sense. I am just too spoiled with the low hanging fruit. POF was a total bomb but I only focused on young girls. Already canceled my account there, so I am done with that.

Fot the last 3 months I have ODed on my "tomboy princess" but she is on her period this week so I may try to venture out. I lost the hot 19 year old stripper I was chasing (post #8028). That was a long shot anyway due to GPS. I am still txting with the older grad student / model in post #8033 and hoping to meet her this week.

[Grumpyinva]

He also mentions match.com and skating the fine line between regular dating of MILFs and being a "helper" to them. I would even take that a step further and say that match and other dating sites might even be better than an SD site for meeting hot MILFs. The "helpable" ones will be easy to spot with the income and age requirements they choose when they sign up.

The benefit of finding them on regular dating sites is that there is a good chance that they are still relatively unspoiled. If they are 40+ and signing up for an SD site because $60 k a year in their regular job just isn't enough for them, they've already got a sky-high list of things in their head they are entitled to in life above and beyond what they actually work for. I guess I'm somewhat forgiving of that in a 20 year old, and I just feel like a 40 year old should be past that sense of entitlement by her age, and have grown into a somewhat more reasonable, realistic person.

JeezLizard,

I have to admit, I have never had success at using the regular dating sites for SBs, though part of that is my own bias. If I'm on an SD / SB site, I figure we all know the score, and I expect that $ will be involved, at some stage. If I'm dating a "regular" girl, and she has emergencies and tries to hit me up for cash, I tend to dump her immediately. I know that that doesn't exactly make sense, given my hobbying habits. I just feel like a girl from PoF or OKCupid is changing the rules of the game if she starts trying to get my cash. However, you're right. If you can identify them, and open with that expectation, it might be a very interesting hunting ground. I hope you'll share if you find good methods to convert them!

I have had success in very limited circumstances on finding an SB in regular activities, though I was 20 years younger at the time, and married. The longest lasting was on a ski trip, where the trip captain was, without a doubt, the biggest be*tch on the bus, but she had absolutely perfect blonde hair down to her waist, and exactly the sort of curves I like. After she managed to offend me and most of the bus (at which point I decided not to take her attitude personally,) I chatted her up, and found that she was in a relationship with a deadbeat boyfriend, made almost no money herself (so they were living with her parents,) and pretty much saw doing those trips as an escape for a free skiing vacation for herself. By the time we were on the way back, she was curled up with me, and sleeping on my shoulder, and we had a daytime date scheduled for the next week. From her attitude and actions, she was CLEARLY a would-be-gold-digger in desperate straits, but she converted nicely into a travel-baby, with only a few "oh my gosh, my truck broke down. Is there any way you can help me with $1" emergencies now and again. As long as we had some kind of day-trip planned (multi-day ski vacations worked well, in the winter, since my wife had no interest in skiing, so they were my escape from the house,) or at the very least a date at a pricey restaurant, she was always DTF, and, despite having my actual contact info from the trip where we met, she never caused any drama for me at home, and we had a fairly regular "thing" for a couple of years. 20 years later, she still touches base with me, although I haven't been as available for her in recent years. Nevertheless, although I've read here about scouting them at wal-mart, I have never had success in that. I tend to either think of it as a regular pick-up when I get a number "in the wild", at which point I'm offended if she starts hinting that she needs cash. I really need to adjust my attitude on that, and stop ignoring potentials!

[JZLizard]

I think this is extremely insightful. I have been generally focused on the 20 ish girls (and probably will continue to be) but occasionally I see one of a more ripe age and think that I should give it a try. I am going to use this approach on the next one!

Didn't copy the whole quote for sake of brevity, but I think your reasoning of the MILF thought process really makes sense (that's a scary thought right there).

He also mentions match.com and skating the fine line between regular dating of MILFs and being a "helper" to them. I would even take that a step further and say that match and other dating sites might even be better than an SD site for meeting hot MILFs. The "helpable" ones will be easy to spot with the income and age requirements they choose when they sign up.

The benefit of finding them on regular dating sites is that there is a good chance that they are still relatively unspoiled. If they are 40+ and signing up for an SD site because $60 k a year in their regular job just isn't enough for them, they've already got a sky-high list of things in their head they are entitled to in life above and beyond what they actually work for. I guess I'm somewhat forgiving of that in a 20 year old, and I just feel like a 40 year old should be past that sense of entitlement by her age, and have grown into a somewhat more reasonable, realistic person.

[Dsprdo]

JeezLizard,

They expect higher pricing for the same reason that you expect to get a higher salary each year in your job, even though that clearly doesn't apply to the market, here. If you throw out $ or $1. 5 into an early email, it's just not going to be that interesting to her, and she may reject you out of hand, even though it would be a fair representation of her market value in this arena.

The MILFs tend to have less folks interested in them, and they're less approachable, so you have comparatively little competition for her attention, and she has already decided that you're someone she would probably date for free, so that's usually the point at which they are ready to be talked into setting up a second date.

I think this is extremely insightful. I have been generally focused on the 20 ish girls (and probably will continue to be) but occasionally I see one of a more ripe age and think that I should give it a try. I am going to use this approach on the next one!

Didn't copy the whole quote for sake of brevity, but I think your reasoning of the MILF thought process really makes sense (that's a scary thought right there).

[JZLizard]

JeezLizard,

I liked your breakdown of the 150 k per year mentality. Stunningly accurate. Then they wonder why they're struggling, with so much "earnings potential".

I disagree on the MILFy perspective, though: I don't think the MILFs are intentionally there to build their egos or put the guys down.

My perspective on MILFs as SBs is probably distorted based on what others have reported here in this forum. In terms of SBs, I've never even had or pursued an SB in that age bracket, so I cannot claim first hand experience with older SBs. I just know that sometimes they contact me through the SD sites, and often times the stuff they write regarding their expectations, their limitations, etc. Is so ridiculous that I guess I've formed a jaded view.

For the record, if the early 30's single mom type counts as MILF material, then let me say some of my best fucks ever, and some of the girlfriends I've cared most for fell into this category. The type I was talking about is usually closer to or over 40, and seemingly very demanding in their expectations and their own sense of entitlement for a lifestyle beyond what they've earned via their own talents. In other words they do not have the physical attractiveness of a 20 year old anymore, yet they seem to demand more.

But as I said, I can only judge them based on how they interact with me in chatting, since I'm uninterested in them as SBs. I just feel that a woman that age should have her shit together well enough by age 40 that it is somewhat arrogant to expect to be taken care of, and I feel it's particularly arrogant of them to consider themselves "sugar baby" material. Maybe they are a baby to an 85 year old, but I doubt that's what most of them have in mind. I'm no spring chicken myself, but I'm in great shape for my age and thankfully still physically in the ballpark that many half my age would still consider dating even with no sugar on the table. So, when one of these cougar types who closer to my age contacts me and says something like "you seem like what I've been looking for" or similar, I could almost take offense to it if I tried.

But yes I see where you're coming from about how offering $ to a cougar isn't going to pique her enthusiasm when she's already got a decent job. The fact that lower amounts of money do not grab their attention I believe is one reason they are often perceived as GPS. And, out in L. A. Where HWG reports a lot of these types, I always envision these housewives of Beverly Hills types who are simply career-gold diggers and have never known anything different. As I said I have very limited exposure to that type of SB.

[Donwhite]

I have not had any luck at all lately. I haven't met up with a SB twice since the tilted kilt waitress that I was seeing and I took her for granted. I miss being able to text her and have her come over and play for $120. I had an Ole Miss student message me that she was going to be in town this weekend and would like to meet me. I messaged her and said sure we can grab breakfast or brunch this weekend and do a meet and greet. I talked and texted with her a little and the day before she said I usually require $350 to meet for a date, but since I contacted you first could you give me $200. I said no thank you and good luck. I really wanted a Mississippi baby. Mississippi women are incredible and they redshirt Miss Americas at Ole Miss. Oh well. The game has been frustrating lately and I need a release.

[Grumpyinva]

JeezLizard,

I liked your breakdown of the 150 k per year mentality. Stunningly accurate. Then they wonder why they're struggling, with so much "earnings potential".

I disagree on the MILFy perspective, though: I don't think the MILFs are intentionally there to build their egos or put the guys down. As someone who tends to prefer MILFs to the 20-somethings (although I've been making some exceptions to that this year. The 20-somethings are just MUCH easier to land,) the ones who are serious are VERY interested in keeping their SD happy, knowing that he has access to a good supply of 20-somethings who are hungry. The difference tends to come into when you make a $ offer to a MILF. If you're 21, and working at McDonalds, and someone offers you $1 or $1. 5, that's a really big deal. She just made 2-3 days of income, just for hanging out with a guy who's treating her better than her boyfriends have, plus she gets to feel the thrill of being "bad".

Once you're in your 40's, 2-3 days of income would still get their attention, but these are women who will normally be making upwards of 60 k per year, and $1 just isn't as exciting. They expect higher pricing for the same reason that you expect to get a higher salary each year in your job, even though that clearly doesn't apply to the market, here. If you throw out $ or $1. 5 into an early email, it's just not going to be that interesting to her, and she may reject you out of hand, even though it would be a fair representation of her market value in this arena.

On the other hand, girls who are 40+ do not expect to be going out with hot, washboard-abs surfer dudes, either. They won't be in the same condition as they were in their 20's, but you're exactly the kind of guy they would regularly date, anyway. If you have decent game, you can spin it as helping with a few things, while dating a very appreciative lady who makes herself available for you, while honoring your need for discretion. To be honest, it's not that easy to find affair-quality women who won't introduce drama at some point, but if you're in the $1. 5 range, and talk to the MILFs pretty much as you would if you were trying to pick them up on a regular dating site, by the time you're at dinner and they ask about your budget and expectations, $1. 5 will sound more like icing on the cake, plus they will not generally consider trying to replace your spouse or SO, because they have a more practical mindset, and they don't want the arrangement to end. Mind you, this only applies to the realistic ones, who realize that the very high rollers aren't going to be interested in MILFs, so their top expectation is a fairly regular guy who will be interested in them, appreciative of them, and who will add a little sugar to the mix.

So my best approach with them is to simply chat them up exactly as if you were on a regular dating site, politely defer any attempts to negotiation via email "I'd rather discuss specifics in person, after we see if we have chemistry," set up a date and make sure you've gotten their number, play a decent text-game with them with a once-a-day-at-most chatty little "Hey, how'd the _ work out today? BTW, I booked our table for Friday, so we could get the good one, by the window" stuff, and otherwise ignore them, until they try to engage you, then give them your full attention for the 10-30 min it takes her to tell you about her day. By the time you get to the date a few days later, they feel comfortable with you, and, again, you treat it exactly as a regular Match.com date, until they ask you about your experiences on the site, which is your cue to roll your eyes and complain about the hordes of 20-somethings that just don't have a clue what life is about, and then ask her about whether she's found any worthwhile guys so far. The MILFs tend to have less folks interested in them, and they're less approachable, so you have comparatively little competition for her attention, and she has already decided that you're someone she would probably date for free, so that's usually the point at which they are ready to be talked into setting up a second date. When they ask about expectations, you can comfortably float the $1. 5 "for when we reach that stage in the relationship," and then let her talk herself into accepting it, since she's not going to reject it out of hand at that point. MOST of the time, they'll quickly suggest that the second date could include some private time together, "if you're interested". Make sure the second date happens relatively soon (before they lose their nerve,) and you're in.

Okay, yes, that's a lot of "work", but it tends to result in a reliable MILFy SB who's fine at $1. 5 (even if she would've rejected that, up front,) and who won't have a second thought about starting early in the day, and staying overnight for that. One of the hardest parts, though, is finding one that you're attracted to, since the pool of MILFs is much smaller than the pool of younger SBs, but it's already a given that trying to groom a SB is harder than just wandering over to BP, with significantly more return, if things work out well.

And I still wish I had Hollywood's powers to keep a stable of attractive SBs at $1 each, but, for now, I'm on the much lower-numbers and slightly higher-cost list!

Female business logic is funny. I once met a stripper who was only a few days into her new craft. Even though she was new, yet said she would make over $150 k that year. I have no problem believing that amount for a top notch Vegas stripper, but this girl wasn't in Vegas and wasn't in that league. After talking to her I understood where she got her numbers. She had a couple of nights that were in the $400-500+ range. By her logic, she would be able to do that every night once she got the hang of the job. It didn't dawn on her that her most profitable nights were weekends only, or that she was getting more interest for being new at the club, or that with every passing day she grew a little older and worn and her value would decrease rapidly. She also didn't take into account her total sales didn't account for her club fee or what she would need to account for in taxes, even if she was a magical unicorn and landed $400-500 per night at that particular club.

It's the same with many SBs, they start out with stars in their eyes, disappointment will set in later. Some of those SBs will become full-on hookers, some of them will leave the scene. Some of them don't really come looking for a specific amount as much as a combination of (A) they don't like to work hard and they haven't needed to thus far in life because of their looks and (B) there is an innate female desire to know their "worth". They love to know how they compare to other women, its a game of "how much can I get for my vag". I think after a certain age they subconsciously realize they are no longer competitive with the young hotties, and this is why we see these MILF cougar types with completely unrealistic expectations -- they don't even really want sex anymore and they've mostly given up on reality, so it's become more like a game to see if they can boost their own ego by damaging a male ego somewhere.

[JZLizard]

This site grades apps on how well they protect the user's privacy. BTW is anyone using the SA app on their real smartphone?

The issues I was speaking of did not entail the SA app itself being malware, it was a general statement about Android apps and the general security issues around them. Of course, SA is not going to intentionally put malware in their app, but all it takes is one accidental misstep from the developer of the app and the door is open for other apps from non-reputable sources to do things with data from the SA app you may not want. The situation at Apple is locked down much better, that's all I meant.

[FotoGuy1970]

Earlier this week, I was contacted by a POT who seemed like she was very interested. Sounded like she needed cash badly due to her situation. Was down for the physical relationship of being a SB. In fact, she was really pushing hard to meet me, wanted to know what she should wear, what I liked, etc.

I arrived at the M&G spot. After the time of the meeting has come and gone, she still hasn't arrived. I go ahead and leave and I text her to find out what happened. She immediately turned judgmental. Judging me on pretty much everything she had learned about me to that point. The funny thing is is that I really wasn't all that interested her, I was just coming to the M&G just in case things were better in person than they had been up to that point. All she did was waste my time, gas money, and burned a bridge. The mentality of some of these girls boggles the mind.