• Home
  • Reviews
    • Flight Reviews
    • Hotel Reviews
    • Lounge Reviews
    • Trip Reports
  • About
    • Press
  • Contact
  • Privacy
  • Award Expert
Live and Let's Fly
  • Home
  • Reviews
    • Flight Reviews
    • Hotel Reviews
    • Lounge Reviews
    • Trip Reports
  • About
    • Press
  • Contact
  • Privacy
  • Award Expert
Home » Travel » The Aging Playboy, The Prada Bag, And The Inflight Romance Scam
Travel

The Aging Playboy, The Prada Bag, And The Inflight Romance Scam

Matthew Klint Posted onJune 6, 2026June 7, 2026 16 Comments

I really felt sad for my seatmate, who was engaged in a frenzied WhatsApp conversation on a flight up the California coast with his “girlfriend” that was impossible for me to avoid and left me very thankful that I am out of the dating game…

My Seatmate’s WhatsApp Romance Drama Screamed Scam

This was on a flight from Southern California to San Francisco on an Airbus A320 jet, with 3-3 seating in economy class (my upgrade did not clear and his did not either). We were seated in the exit row and the middle seat between us was open.

As I settled into my seat, the man was already seated and had quaffed down a Buffalo Trace Bourbon mini…it wasn’t clear (yet) if he brought it onboard or a flight attendant gave it to him, but he did have a blue plastic United cup with some ice in it.

This man looked to be around 75 years old, but was doing to his best to look youthful, with his hair dyed a jet black color. It was also clear that he had cosmetic work done…I just don’t understand why people inject fillers into face, but that’s certainly his prerogative. He was wearing a dark suit with an open collar and had several rings on his finger.

He was holding his phone out in front of me and typing furiously. I don’t make a habit of reading other people’s messages, but it virtually impossible to avoid doing so here by the way he angled the phone, placing it directly into my line of sight.

He was boasting about how great his tongue game was…and well, you get the idea.

All of a sudden he slammed his fist down on the armrest. I was looking out the window but turned back and saw that his “girlfriend” had sent him a demand. “Did you bring my gift?” as he asked.

He assured her that he would be bringing her the Prada bag she wanted.

The chatting continued via WhatsApp, but I turned away to focus on my work.

As the flight progressed, he pulled himself out another bourbon mini from his bag and poured it himself. During the beverage service, he ordered a Stella Artois beer. Odd mix, no?

I could tell he was upset about something and he neared SFO I looked over again at his phone and saw they were arguing about her gift. She said she no longer wanted the Prada bag and wanted an iPhone 17 Pro Max instead. And that he should mail it to her.

The guy was pleading with her to meet in San Francisco, as planned.

Do I tell him that “Jasmine” is probably not even a real woman? That “she” is more likely a fat dude in his mother’s basement trying to scam him?

He was upset…so upset that he pulled out another bourbon from his bag and downed it.

I was so divided. Try to talk to talk to him or let him be, especially because he was either drunk or close to drunk?

He was so busy going back and forth on his phone that I left him alone.

Maybe this guy enjoys this torture or considers the price worthwhile to get a girl that is 45-50 years younger than he is. Different strokes…I’m just thankful I have a relatively stable life with a loving wife and children…and I just hope he goes into these encounters with his eyes wide open because the entire conversation screamed out SCAM to me.

As we got up, I told him, “Best wishes, pal. Be careful out there.” He looked at me and smiled, shaking his head slightly but saying nothing before looking back down at his phone.

Get Daily Updates

Join our mailing list for a daily summary of posts! We never sell your info.

You have Successfully Subscribed!

Previous Article Barking “Service Dog” Ruins My United Airlines Redeye Sleep
Next Article Allegiant Bought An Airline To Sell A Credit Card

About Author

Matthew Klint

Matthew is an avid traveler who calls Los Angeles home. Each year he travels more than 200,000 miles by air and has visited more than 135 countries. Working both in the aviation industry and as a travel consultant, Matthew has been featured in major media outlets around the world and uses his Live and Let's Fly blog to share the latest news in the airline industry, commentary on frequent flyer programs, and detailed reports of his worldwide travel.

Related Posts

  • flight cancellation refund dot

    Your Cancelled Flight May Not Count As Cancelled

    June 7, 2026
  • Air Canada A321XLR

    Air Canada Joins The Long-Haul Narrowbody Club

    May 31, 2026
  • Mediterranean soft 2026 Pegasus Airbus A321 in Rome

    The Mediterranean Is Soft This Summer

    May 24, 2026

16 Comments

  1. PeteAU Reply
    June 6, 2026 at 4:08 pm

    I have an acquaintance who’s being fleeced by a woman in Thailand. She’s real, he travels there every few months to see her, but she’s obviously a grifter. His friends are dismayed; a mutual friend has told him what everyone thinks, but he refuses to see. My take on the matter is that people have said their piece, and it’s up to him to take action. He’s a grown man in his 60s, not a kid who needs to be protevted from a predatory adult. Sometimes we just have to walk away…

    • 1990 Reply
      June 6, 2026 at 6:55 pm

      I mean, at least he’s going to Thailand; the crab curry and mango sticky rice alone is worth the trip! (Besides, Suvarnabhumi has so many decent lounges!)

  2. derek Reply
    June 6, 2026 at 4:24 pm

    I just looked it up and see there is an AARP Fraud Victims Support Group online. Just hope a scammer won’t also join.

  3. 1990 Reply
    June 6, 2026 at 6:50 pm

    “quaffed down a Buffalo Trace Bourbon” … well, at least he’s a gentleman. Bah!

    • 1990 Reply
      June 6, 2026 at 6:52 pm

      “tongue game” … oh, my word!

      Were you flying Aer Lingus? *nudge nudge*

  4. Güntürk Üstün Reply
    June 6, 2026 at 9:48 pm

    The young woman in the photo accompanying this article is truly captivating. It’s a fact that, looking out the window of the plane she’s traveling on, she’s not thinking about life’s tragedies [lost/unrequited love, malignant disease(s), premature old age…]. By the way, for those who might be interested, here’s a short travel poem from me↓

    While gazing at the skies, she asked the air travel with her eyes,
    “How do you manage to stay so young all the time?”
    “By constantly renewing myself, oh brainy beauty” the air travel replied.

    ©Güntürk Üstün (2026)

  5. Christian Reply
    June 6, 2026 at 9:49 pm

    “Aging Playboy”? At 75, I think that train left the station a couple of decades ago although it’s kind of you to couch things in such terms.

    • This comes to mind Reply
      June 7, 2026 at 7:01 am

      Men who are fit (mentally and physically) and who don’t vainlt fight the aging process find their attractiveness to younger woman surprisingly strong. If you are much younger, just wait. If you’re near that age and don’t find younger woman attracted to you, that’s your failure. Of course, the guy described sounds like he’s making very wrong moves.

      • 1990 Reply
        June 7, 2026 at 7:18 am

        (Yeah, keep telling yourself that… maybe in Ohio… but not NYC or LA…)

  6. Güntürk Üstün Reply
    June 6, 2026 at 10:00 pm

    This interesting article suddenly reminded me of the 2019 French mystery and thriller film “Seules Les Bêtes (Only The Animals)”…

  7. Maverik Reply
    June 7, 2026 at 1:18 am

    >I’m just thankful I have a relatedly stable life with a loving wife and children…

    For now, and probably for near future, but you never know if you find yourself in a same shoe as this guy when you turn to 75.

  8. Kyle Prescott Reply
    June 7, 2026 at 9:01 am

    He’s 75, let him spend his money however he wants. IF he has kids they deserve nothing. Let him enjoy the time he has left, it’s later than you think.

    • This comes to mind Reply
      June 7, 2026 at 12:35 pm

      I don’t think anyone here wants to reign in his parade. But, Matthew (and me, too) is worried about him flushing money down a toilet and regretting it later. I have no problem with a sugar daddy relationship. It’s not for me, but if the guy is happy and has no regrets when it ends, more power to him. If that relationship is one-sided and he feels used after it ends, that’s sad. I wish that on no one not currently living in the White House.

  9. Thomas Cooper Reply
    June 7, 2026 at 11:29 am

    “A fool and his money are quickly separated.” -Benjamin Franklin

  10. Maryland Reply
    June 7, 2026 at 12:35 pm

    Attractive men are intelligent, confident and humorous at any age. Be that guy and genuine happiness will find you.

    Ignore the alley cats that only want to date your wallet

  11. PolishKnight Reply
    June 7, 2026 at 4:34 pm

    I feel bad for him. I have heard of this scam and it’s always them wanting the latest iphone because they’re extremely expensive and easy to trade/cash in Thailand.

    It’s like Jack Reacher (Tom Cruise) version said in the film: “If you’re not a prostitute, then I absolutely cannot afford you.”

    That said, sometimes I like to tease and play the scammers. He should have said he sent it and instead sent a blank FedEx envelope but put a used iPhone 5 inside of it making it look like a mistake from the shipper. Oh, and have it locked.

    That said, one of the great things about having travelled is I know… er, the scams, stories, and er, alternatives to being scammed in bad relationships…

Leave a Reply

Cancel reply

Search

Hot Deals

Note: Please see my Advertiser Disclosure

Capital One Venture X Business Card
Earn 150,000 Miles Sign Up Bonus
Chase Sapphire Preferred® Card
Earn 100,000 Points
Capital One Venture X Rewards Credit Card
Capital One Venture X Rewards Credit Card
Earn 75,000 Miles!
Capital One Venture Rewards Credit Card
Capital One Venture Rewards Credit Card
Earn 75,000 Miles
Chase Ink Business Unlimited® Credit Card
Earn $750 Cash Back
The Business Platinum Card® from American Express
The Business Platinum Card® from American Express
Earn 120,000 Membership Reward® Points

Recent Posts

  • boutique hotel LE Maimi conference Hilton Curio Collection concierge activation
    Inside L.E/Miami: The Invite-Only Show For Posh Hotels June 7, 2026
  • flight cancellation refund dot
    Your Cancelled Flight May Not Count As Cancelled June 7, 2026
  • a blue and orange airplane on a runway
    Allegiant Bought An Airline To Sell A Credit Card June 7, 2026
  • inflight romance scam
    The Aging Playboy, The Prada Bag, And The Inflight Romance Scam June 6, 2026

Categories

Popular Posts

  • a black credit card on a blue keyboard
    Bilt Rent Day: TAP Air Portugal Transfer Bonus Of Up To 125% June 1, 2026
  • a room with chairs and a picture of an airplane
    Review: Lufthansa Lounge London Heathrow (LHR) May 28, 2026
  • World of Hyatt award chart changes
    Final Call: Hyatt Just Blew Up The World Of Hyatt Award Chart May 19, 2026
  • SWISS Senator Lounge Zurich Review
    Review: SWISS Senator Lounge Zurich (ZRH) May 29, 2026

Archives

June 2026
M T W T F S S
1234567
891011121314
15161718192021
22232425262728
2930  
« May    

As seen on:

facebook twitter instagram rss
Privacy Policy © Live and Let's Fly All Rights Reserved. Unauthorized use and/or duplication of this material without express and written permission from this site’s author and/or owner is strictly prohibited. Excerpts and links may be used, provided that full and clear credit is given to Live and Let's Fly with appropriate and specific directions to the original content.