Episode 47 · The GaS Digital / Ray Kump Era
Seeking Arrangements (with Wendi Starling)
with Wendi Starling
May 30, 2017 · 1:18:57 · 25 segments, 177 moments indexed
- 1 min
Show intro music and voiceover about Tim Dillon Is Going To Hell examining billionaires, dictators, and CEOs.
1moment
- 0:10Tim describes the show's premise: taking a hard critical look at the people society has decided to hate—billionaires, dictators, CEOs.
- 2 min
Ray Kump's Verizon Fraud Scare and the Morgue Job
#Tim welcomes co-host Ray Kump, who recounts a near-fraud incident with a Verizon headphone order and his bank, leading into a riff about Ray needing a morgue job to finally get a bank account, potato bread warehouse jobs, and check-cashing places.
6moments
- 0:43Ray received a fraudulent Verizon email claiming $600 in headphones were shipping from his account.
- 1:03Tim notes that Ray's bank sent him a fraud alert text, making the story anticlimactic when Ray simply canceled the card.
- 1:25Ray got his first bank account after taking a job at the morgue.
- 1:37Tim reflects that everyone has a personal "morgue job" moment—a challenge that changes their trajectory.
- 1:49Before the morgue, Ray worked warehouse jobs and had to use check-cashing places that charged ten dollars per transaction.
- 2:01Tim jokes that Ray's life story contains so many Netflix documentaries that Netflix has already made them—Bloodline, The Keepers, House of Cards.
- 2 min
Tim introduces comedian guest Wendy Starling, jokes about the show's dark pedigree (pedophile cult episodes) versus this lighter topic of consensual adult sex, and sets up a 'knock on the table' rule for anything she doesn't want to discuss.
4moments
- 2:20Tim notes the show is now discussing sex between consenting adults, calling it a new and gauche direction for the program.
- 2:34Wendy Starling introduced as a hilarious and very funny comedian guest.
- 3:05Tim explains the knock rule: if Wendy doesn't want to discuss something, she can knock on the table and they'll pivot to telling stories about the potato bread warehouse instead.
- 3:22Tim praises Wendy for being open and honest in her comedy act, which he says makes it really funny.
- 3 min
Wendy describes her pre-sugar-baby life in LA: working 40+ hours at Whole Foods, doing comedy at night, and selling vegetables at a farmers market for $120 a day while being sexually harassed by her boss, before moving to New York.
9moments
- 3:51Tim says he always feels like he's working, even doing comedy—it's not fun.
- 4:07Guest describes dating wealthy men as a "fancy girlfriend" situation, a recent development at 35.
- 5:04Working at Whole Foods in LA as a buyer for the whole body department while doing shows every night.
- 5:30Guest sold vegetables off a farm stand on Sunday mornings for $120 cash, a nine-hour day in the heat.
- 5:45Tim asks if she feels like a sucker looking back at those jobs.
- 6:01Guest describes doing the kind of labor "that Mexicans do that people say no one wants to do."
- 6:20The guy running the vegetable stand sexually harassed her constantly with the same line about his wife.
- 6:31Tim compares her pre-New York life to The Grapes of Wrath.
- 6:50A wealthy man she met on Tinder while working at Whole Foods in Tribeca suggested the arrangement.
Whole Foods MarketSeeking ArrangementsLos AngelesAstoriaTribecaUnion Square
- 4 min
Wendy explains how a rich Tinder date first suggested she try sex work, and how she got started selling worn (and masturbated-in) underwear to businessmen, with Ray repeatedly grossing everyone out with questions about bodily fluids.
6moments
- 7:16Tim notes they've discussed children being killed on the show, so her mention of vegetables seven times is what actually disturbs him.
- 7:35The Tinder date—a rich guy in New York—suggests she consider sex work to make money more efficiently.
- 8:13When she says no one would pay her, he insists yes they would, and she realizes how strange it is for someone dating her to pitch that idea.
- 8:41Tim asks if the suggestion planted a seed, and she explains her hesitation based on not looking like a porn star and having short hair.
- 9:47She decides to go for it after a roommate leaves and she needs $1,500 in two and a half weeks.
- 10:06She went on Craigslist willing to have sex for money, since she was already sleeping with multiple people weekly anyway.
- 4 min
Wendy describes turning an underwear buyer into her first sugar daddy by negotiating per-meeting rates, treating it like a business, and reflects on emotionally manipulating him for more money.
9moments
- 12:06Selling worn underwear while temping at a clothing company was all profit, using nice lace pairs.
- 12:18The buyers were wealthy businessmen from the same parts of the city, surprised when she didn't look like a crack addict or cop.
- 12:55One underwear client became a sugar daddy who wanted to see her all the time.
- 13:07Tim asks about pricing: if meeting for 15-30 minutes at $50 for underwear, does the client also pay for her time?
- 13:24She faked having lots of other clients to negotiate better rates, same way she lies on stage as a comedian.
- 13:37She broke down pricing to $50 for 30 minutes of her time, rather than just selling underwear.
- 14:00When he objected to paying for her time, he claimed she was trying to take advantage and said he didn't want to be a sugar daddy.
- 14:26Her response: you're buying underwear from Craigslist from a stranger, so fuck you, pay me.
- 14:44Looking back, she emotionally manipulated him beautifully and got more money out of it.
- 6 min
Wendy details setting up a joke sugar-daddy profile, then her real Seeking Arrangement profile, how she screens genuine messages from copy-paste scams, and frames her arrangements as a modern 'concubine relationship' with wealthy men, plus discussion of whether young college-age people should get involved in this world.
10moments
- 15:03Tim set up a Seeking Arrangements profile as a joke, claiming to be worth five million dollars.
- 15:28The site requires a monthly fee to message people, which Tim refused to pay.
- 15:48Profiles list lifestyle expectations like 'reasonable,' 'pragmatic,' or desires to travel with wealthy men.
- 16:13Tim asks whether 18 or 19-year-old college students should work at Starbucks instead of using the site.
- 16:35On his real profile, Tim lists his actual age and comedy work with no deception.
- 17:00His pitch: he has no time to date but wants sex and nice dinners, making Seeking Arrangements like an instant relationship.
- 17:29Most messages from men are fake or copy-pasted; real ones mention something personal about her profile.
- 18:03This type of arrangement is essentially a concubine relationship with very wealthy men.
- 18:47She realized immediately that money comes quickly, but had to remind herself not to get rich off it.
- 19:52When there's too much cocaine involved, the sex isn't good.
- 3 min
Discussion of how often the sex is good versus bad, dating guys who aren't attractive only for big money, and one long-term arrangement with a guy who provides access to his lawyers, gym membership, and Ubers.
10moments
- 20:48Tim's guest describes her current arrangement as phenomenal.
- 21:03She hugged up with a guy once who wasn't attractive, but at 35 she expects both of them to go to the gym.
- 21:24Five thousand dollars for a night changes her calculation entirely.
- 21:52Tim asks what the going rate is for a one-night stand with a stranger.
- 22:10Her first guy from the seeking site became a friend; he still pays for her gym membership and Ubers.
- 22:25The lawyer sugar daddy provides her access to his attorneys for contracts on big deals.
- 22:44She describes the arrangement as having a really cool rich dad who might want to have sex with you at some point.
- 22:58Tim's guest uses her previous boyfriend's allowance as a marker for what to ask new prospects.
- 23:25Ubers alone run between $700 and $1,000 a week on his card.
- 23:35Tim observes that guys with this level of net worth simply don't care about spending thousands a month on transportation.
- 4 min
Wendy breaks down monthly allowance negotiations, Uber costs as a write-off, not being on-call like a slave, and Tim's characterization of the whole arrangement as delivery-app-style 'pussy Grubhub.'
6moments
- 24:41Tim asks whether receiving an allowance makes her a slave, given that she's also working other jobs.
- 25:15Monetizing sexuality and its potential impact on future relationships in deeper, longer-lasting connections.
- 25:46She's done the younger love and turmoil thing; now she's focused on being successful and getting her own apartment.
- 26:16Tim suggests her concern about dating married men — wanting them to divorce their wives for her — sounds damning.
- 26:57Everything in New York gets delivered: food, booze, and through these sites, sex — she's essentially pussy Grubhub.
- 27:08Tim asks how kinky the sex gets on the site and whether guys use it for kinks they can't ask for from regular dating.
- 3 min
Wendy discusses her sexual openness versus missionary boredom, and Ray's bizarre glass-coffee-table shitting scenario gets negotiated in detail including the need for a week's notice and proper fiber intake, alongside a rich-kid tangent about a Berkshires mansion.
9moments
- 27:33Tim's date says she seems like the type who'd do crazy sex stuff on an airplane.
- 27:50She explains that regular missionary isn't enough—she wants to get tied up and do extreme things.
- 28:07Her boyfriend only wants to hold her close in missionary, which she finds boring, leading to the mention of 'glass coffee table stuff.'
- 28:21Tim asks what the glass coffee table fetish is, and she reveals it involves shitting on the glass while someone's underneath.
- 28:46The conversation shifts to whether she'd do it if a hedge fund manager was under the table pleasuring himself.
- 29:05She says she'd need a week's notice and wants to know how much money first.
- 29:16Tim goes on a tangent about rich people in the Berkshires who disown their own wealth while enjoying inherited mansions.
- 29:57Tim notes her practical approach: weeks of notice to plan the logistics and timing with proper nutrition and fiber.
- 30:28The conversation turns to pegging, which Tim notes is becoming a mainstream request from men.
- 5 min
Wendy talks about pegging one client, her submissive-in-private-alpha-in-public dynamic, and a friend's warning about sex, money and drugs mixing into dark places, followed by discussion of how she vets clients over lunch before ever meeting privately.
7moments
- 31:26Tim asks who holds the dildo when she pegs guys, leading to revelation she's only done it once.
- 32:25Friend who's a sex addict warned Tim that mixing sex, money, and drugs can get very dark.
- 33:09She says she's never been in a bedroom with someone who creeps her out because she meets them first.
- 33:57Her process: meet for lunch first, then negotiate allowance and frequency with potential partners.
- 34:35One guy emailed that he normally only dates women with their own apartment in the West Village, while using a sugar dating site.
- 35:01The guy showed up much uglier than his pictures and tried to lowball her with a calculated hotel-room budget.
- 35:24She has a regular client who stays in hotels and leaves the city afterward, giving her free luxury accommodations.
- 3 min
Wendy recounts a disastrous lunch meeting with a cheap, rude client who tried to deduct hotel costs from her allowance and got hostile about her age, ending with her storming out of Union Square Cafe declaring she'd rather clean toilets for $7 an hour.
8moments
- 35:56Potential sugar daddy suggests an hourly hotel instead of an overnight stay.
- 36:16He threatens to deduct the hotel fee from her allowance if she won't agree.
- 36:42Tim notes the guy looked disgusting and was trying to play a dominant angle at lunch.
- 37:11She explains she has comedy income and decent self-esteem, so she's not desperate.
- 37:28Guy starts yelling about her age and whether she'll find anyone to give her five grand a month.
- 37:54Tim points out he was yelling about money in a restaurant instead of being discreet.
- 38:12She stands up and announces loudly she'd rather clean toilets for seven dollars an hour, then throws her napkin and leaves.
- 38:27Tim defines that as a real New York moment—meeting a guy from a website who suggests an hourly motel, then walking out.
Rockefeller CenterUnion Square Cafe
- 2 min
Ray's Craigslist Hooker Story at the Marriott
#Ray recounts losing his virginity to a Craigslist sex worker at a Marriott for $150, including an awkward moment where she wouldn't reciprocate oral sex, and a separate story about a hooker who kissed him.
6moments
- 39:00Ray describes finding a woman on Craigslist who was chubby and mostly just laid there.
- 39:27Ray explains that sex workers on Craigslist always hint at GFE—girlfriend experience—but don't actually deliver it.
- 39:39Tim notes that one Black woman hooker actually kissed Ray because he was sweet and nice to her.
- 39:52Ray recounts asking her to blow him, but she refused and asked him to go down on her instead.
- 40:07Ray admits he didn't reciprocate at the time but says now he would eat her asshole without hesitation.
- 40:19Tim suggests Ray should have locked her down after they both came, while he's in better shape now.
- 1 min
Bargain Basement Hookers Riff
#Tim riffs comedically on cheap, crapshoot Craigslist encounters — island girls, trafficked Ukrainian women — as a dark comedic bit before turning back to Wendy about judgment from other comics.
4moments
- 40:45Tim describes the luck of encountering a non-English-speaking sex worker from the islands with specific physical attributes.
- 40:55He details another scenario: a recently trafficked Ukrainian woman who complies out of fear.
- 41:08Wendy asks if Tim ever gets judged by other comics and people for openly discussing this behavior on stage.
- 41:25Wendy mentions publishing an article for Women's Health magazine about her sugar daddy.
Women's HealthUkraine
- 4 min
Wendy discusses writing about her sugar daddy for Women's Health and describes attending a paid sex party run by a Dom acquaintance, including the cocaine, the loft setting, other sub women, and a comedian client who wanted to come to her show.
9moments
- 41:42Women's health magazine editor asks Tim to write dating expert articles based on his sex party stories.
- 42:10The sex parties are paid events—a Dom friend offers Tim money to attend after he says he's busy temping.
- 42:28Parties happen in Manhattan lofts with multiple female subs; men pay a cover fee to attend and select partners.
- 42:54The female participants arrive early, have dinner, do each other's makeup before the paying guests show up.
- 43:21Cocaine is heavily available at these parties, along with an open bar and any drugs the guests want.
- 43:47Paying guests point out which women they want to play with; the Dom coordinates the arrangements.
- 44:20Tim stopped attending after the head Dom got drunk and invited a random guest to join them at an afterparty diner.
- 44:40The random guest turned out to be a comedian who later wanted to come to Tim's comedy show, which she refused.
- 44:53The comedian guest came inside her asshole without consent, making her never want to see him again.
sex partieswomen's health magazine
- 3 min
Wendy talks about wanting to watch two guys together, why she keeps her arrangement world separate from real dating, why she thinks this lifestyle isn't right for young/unformed people, and warns off would-be listener orgy requests.
8moments
- 45:23Tim explains he's attracted to two men together at parties and wants to watch them have gay sex.
- 46:01He urges listeners not to email about orgies, especially not to Wendy.
- 46:17Dating someone now has brought exciting experiences, but New York comic women are cooler about it because they understand how expensive the city is.
- 46:41Tim advises against pursuing this lifestyle in college because people don't know what they're doing yet.
- 46:57He argues young people should live first and build a sense of self before getting into group sex.
- 47:21Tim questions whether some women with rough backgrounds might benefit from connection with successful older men.
- 47:48His guest counters that even women in their 20s aren't developed enough to make major life decisions, let alone get married.
- 48:05Tim gets distracted mid-sentence, mentioning his thighs are sweating.
- 2 min
Wendy describes wealthy clients' lockboxes full of prescription and street drugs and morning Adderall habits, while Ray jokingly angles for whether he could trade sex for Adderall.
4moments
- 48:46Tim describes dating highly successful guys who kept lockboxes full of both illegal street drugs and prescription pills.
- 49:11Tim tried Adderall once and thought his heart would explode; refuses to get used to it despite the casual availability.
- 49:27Tim asks whether he could fuck for Adderall, given how much of it one guy had lying around.
- 49:39The other person argues Tim is out of his mind, that no one's actually going to pay him anything for sex.
- 6 min
Tim shares a personal story about paying a closeted-era hookup with a fireman trainee for discretion, leading into a discussion with Wendy about how straightforward monetary arrangements compare to the games played by women chasing rich husbands on the Upper East Side, and the double standard/backlash women face for it.
7moments
- 50:03Tim recounts meeting a fireman trainee in a cheap hourly hotel, paying him $100, and the guy insisting he wasn't gay before anything happened.
- 50:29Financial desperation may push people into transactional sexual situations they wouldn't otherwise consider.
- 50:57Discretion is a major reason people seek paid arrangements rather than navigating the social complications of conventional dating.
- 52:16The discretion involved in paid arrangements includes not being bothered at odd hours and understanding the terms upfront.
- 53:51Tim weighs in on a friend who's a sex addict, fucking five or six girls simultaneously while wanting to become a father.
- 54:37The friend should not have a kid if he's incapable of monogamy and continues cycling through drugs, sex, and threesomes.
- 54:57Tim refuses to entertain the idea that someone juggling multiple partners and addictions would be a good father, calling it wrong.
Mark HotelUpper East SideWendy
- 2 min
The Sex-Addict Friend Who Wants a Kid
#Tim describes a promiscuous, drug-using friend who wants to be a father despite his lifestyle, and the group debates whether he should have kids, suggesting he volunteer as a Big Brother instead.
7moments
- 55:48Wealthy people pay women for affection while struggling with sex and drug addiction, mistaking the chemical high for genuine connection.
- 56:12Many people have kids for the same addictive reason—wanting something to love them because they feel so alone.
- 56:22The friend says he wouldn't feel like he missed out without marriage, but would regret never being a dad—a selfish framing of parenthood.
- 56:39Tim points out that a guy who pays for women and does drugs constantly might not be the best candidate for raising a child.
- 57:05The friend is 27, has attended sex addict meetings, and has destroyed relationships because he can't commit.
- 57:19Tim's advice: if you're that type of guy, be that guy, but don't bring a kid into it.
- 57:38Tim jokes about being a Big Brother himself, describing a mentorship that involves hiding knives and teaching kids not to be rats.
- 4 min
Wendy reflects on lessons from wealthy clients — their relentless work ethic, casual attitude toward money as 'not even real,' and whether she secretly wants deeper relationships with any of them.
8moments
- 58:27Wealthy clients work 12-14 hours a day constantly, motivated and hyper-driven rather than coasting on inherited money.
- 59:09Tim notes the appeal of money in New York—taking cars places, wearing nice shoes—without framing it as evil.
- 59:24Wendy jokes that working with rich clients has taught her she's a full-blown sociopath.
- 59:40Rich people reach a point where they say money isn't even real, just energy, which changes how they relate to it.
- 1:00:12Tim asks if Wendy ever spooned with her clients, leading to her relief that the question wasn't darker.
- 1:00:35Wendy describes sometimes going to dinner with clients without sex, just hanging out together.
- 1:01:08Tim probes whether Wendy ever wants more from these relationships or if she's shut off that instinct entirely.
- 1:01:21Wendy admits to occasional twinges of wanting more, but realizes dating someone wealthy would require being around constantly and sacrificing her comedy work.
- 5 min
Wendy explains findom/pay-pig dynamics where men pay just to be insulted and sent demands for money, and Ray comically tries to get involved as a potential pay pig himself.
12moments
- 1:01:52Financial domination explained: guys get off when someone texts them demanding money, leading to orgasm.
- 1:02:10The term 'pay pig' describes submissives who send money after being verbally degraded and humiliated.
- 1:02:39Tim volunteers to participate in financial domination, then backtracks when the actual mechanics are explained.
- 1:03:30Emotional manipulation can extract significantly larger amounts of money from wealthy submissives in these arrangements.
- 1:03:44These are millionaires spending discretionary income on consensual sexual relationships, so there's no guilt involved.
- 1:04:30A documentary crew followed her for a year and a half starting when she first moved to New York, capturing her early career.
- 1:04:56The documentary includes footage of her filling out applications to work as a prostitute because she needed money.
- 1:05:27A lawyer is reviewing all contracts for a documentary that's seeking venture capital investment with no risk.
- 1:05:50The primary investor is someone she met at Equinox gym on Lex and 63rd through a connection from the website.
- 1:06:11Her mother found out about her work through a published article and doesn't care, having made similar financial choices herself.
- 1:06:38She contrasts herself with other girls who demand shopping, jewelry, and fancy dinners—she just wants money for work.
- 1:06:49Her approach: get some sex, take the extra cash to support her independent work without requiring constant gifts.
- 5 min
Wendy compares her situation to her mother leaving her father for a wealthier man, argues for legalized/regulated prostitution to protect trafficking victims, and reveals a documentary crew followed her for a year and a half that's now being shopped with investor backing.
10moments
- 1:07:01Tim's mother was a high-end sex worker in the 1970s at the Plaza Hotel and made enough money to own serious stock.
- 1:07:16Tim treats sex work as a business like any other—some people do it well, but young people without development shouldn't jump in unprepared.
- 1:07:56Legalizing prostitution makes sense for high-priced escorts, but most prostitution involves trafficking and exploitation from third-world countries.
- 1:09:09Tim argues legalization would actually reduce trafficking because victims could report abuse to police instead of staying in the shadows.
- 1:10:18The guest describes her arrangement as simple and above-board, with clients free to end things anytime.
- 1:10:41She's experienced heartbreak from clients stopping contact, which hurt more than when they simply moved on to other women.
- 1:10:57This kind of arrangement could only work with wealthy men who have time constraints but want something consensual and real.
- 1:11:16Every now and then the guest will sleep with a struggling comedian just to make sure she's still got it.
- 1:11:39Tim asks about her comedy ambitions; she's pitching her live show Glamour Press to different networks and working on two scripted shows.
- 1:11:59A documentary about her is set to release in theaters between October and January, which she plans to tour off once it comes out.
Glamour Pressprostitution legalizationPlaza Hoteldark web
- 2 min
Wendy plugs her podcast Jammers: The Selfish Help Podcast and social media handles; Ray also gives his info and jokes about wanting financial domination clients himself.
6moments
- 1:12:27Tim launches the Selfish Help podcast with Megan Rice and Steven Penta, who dates Christina Hodgson from the Famous Guys We Fucked podcast.
- 1:12:47Original podcast title was rejected: Kids We Fucked, then Kids with a backwards Z.
- 1:12:58The show format involves setting challenges to improve yourself or remove negatives, plus bringing in experts like spiritual advisors for meditation sessions.
- 1:13:21Wendy Starling's social media: Twitter at wendystarling, Instagram wendybird82 (the year she was born).
- 1:13:54Ray Kump offers financial domination services and mentions his card got frozen after getting beaten at Best Buy.
- 1:14:11Ray Kump's upcoming project: guinea pig, findable at RayKump on social media.
Selfish HelpCorinne FisherChristina HodgesonMegan RiceSteven Penta
- 2 min
Tim runs down upcoming tour dates including Poughkeepsie, Newport Vineyards, Denver Comedy Works with Dan Soder, and Zanies in Chicago, plus asks listeners to rate the show on iTunes.
5moments
- 1:14:26Friend's father died at 67; Tim describes him as a great guy who treated them like sons over martinis and drinks.
- 1:15:02Tour bus show sold out in hours; adding Thursday June 15th show as the last one for a while before potentially resuming later in summer.
- 1:15:19Tour bus does ninety-minute show through wealthy NYC areas discussing finance, real estate, and human trafficking while examining what it takes to live there.
- 1:15:40Tim performing June 3rd in Poughkeepsie with Brett Raybould, June 10th at Newport Vineyards in Rhode Island, and June 29th with Dan Soder at Denver Comedy Works.
- 1:16:04Late July appearance at Zany's Comedy Club in Chicago — Tim's first time there and supposedly one of the best rooms in the country.
- 2 min
PO Box Fan Mail and Shannon's Dick Dating Show Date
#The group jokes about setting up a PO box for listener gifts like the Tuesdays With Stories crew gets, then closes with a bit about producer Shannon's upcoming date from a 'dick dating show' and a size comparison joke to end the episode.
6moments
- 1:16:38Tim takes photos of rich people's homes for Instagram, and once photographed a shoe he found on the floor.
- 1:17:22Ralph is working on setting up a PO box for fan mail.
- 1:17:38Tim jokes about soliciting $10 gift cards from listeners to buy Arby's and review it on air.
- 1:17:51Listeners are encouraged to send old books and clothes, not stolen debit cards.
- 1:18:16Shannon hasn't had sex in two years but is meeting someone tonight from a Dick dating show.
- 1:18:38Shannon describes her date's anatomy as being the size of a water bottle.
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