• Video
  • Shop
  • Culture
  • Family
  • Wellness
  • Food
  • Living
  • Style
  • Travel
  • News
  • Book Club
  • Newsletter
  • Privacy Policy
  • Your US State Privacy Rights
  • Children's Online Privacy Policy
  • Interest-Based Ads
  • Terms of Use
  • Your Privacy Choices
  • Contact Us
  • Recalls and Product Safety Alerts
  • © 2026 ABC News
  • News

What Would You Do? Gold-Digging Fiancee Exploits Future Husband

ByALI GALANTE
January 11, 2011, 5:24 PM

Jan. 14, 2011 — -- At Wicked Wolf Tavern, in Hoboken, N.J., a woman in her early 20s and a much older man talk excitedly about their upcoming marriage. "I love you, I love you," Ashley says in between talk of her $20,000 wedding dress and buying a second home in the Hamptons.

Their relationship draws glances from nearby customers, but when her date excuses himself to use the restroom, her affectionate tone changes.

"He is so disgusting! Ugh, I can't wait for him to die already," she gushes to someone on the other end of her cell phone when her fiance is out of sight.

What customers inside the Hoboken bar don't know is that Ashley is an actress and her senior sweetie is also part of our scenario. As we set up our "What Would You Do" hidden cameras at the Wicked Wolf we wondered what would people do when they see someone being scammed this way?

"Marry for money first and for love second," Ashley can be heard saying into her cell phone. But one single diner has heard enough. When Ashley flirts with our actor bartender, the diner asks to be moved to the other side of the bar, far from Ashley's inappropriate advances. When we fill him in on our "What Would You Do" scenario and ask why he wouldn't get involved, he tells us, "Who am I to tell him how to live his life, when he's already lived so much life?"

Gold Digger to Marry Elderly Man

However, not all customers believed they could distance themselves from our couple. Two intrigued co-workers inquire about Ashley and Jon's marriage.

"Oh cool," the male exclaims when Ashley confesses she is marrying Jon for his money. "At least you know what you want."

When our actress continues to explain her motives, the woman says, "I like your style."

At first, the co-workers seem to go along with our actress's ploy and even to condone her behavior.

But their facial expressions betray their feelings, and show shock. When they're alone with Jon, they offer their advice. "Make sure you keep your money," one says. "If you just met her, you don't need to rush," says the other.

Another customer expresses her feelings more bluntly. When Ashley is out of sight, Jon confides in two sisters sitting beside him. "Of course, everyone says she's in it for the money," he says. "She's in it for the money," one confirms. "That's what prenups are for."

However, she also tells him to consider something else -- his happiness.

"As long as you're happy ..." the sister offers. The less vocal sister prefers that her sibling stay silent. But when our couple leaves, she tells the tale to our bartender. "You'd think he'd get a prettier gold-digger! I feel so bad for that guy."

We wondered what would happen if we swapped our gold-digging female for a gold-digging male ...

Watch the scenario unfold Friday at 9 p.m. ET on "What Would You Do?"

Up Next in News—

E. coli outbreak linked to raw milk cheese brand: CDC, FDA

September 26, 2026

Judge in Lindsay Clancy case indefinitely impounds jury questionnaires

September 23, 2026

Simone Biles says 3 masked men stole luxury sports car from Chicago-area home

September 23, 2026

Capt. Chesley 'Sully' Sullenberger shares new details of Alzheimer's diagnosis, his 'last flight'

September 23, 2026

Shop GMA Favorites

ABC will receive a commission for purchases made through these links.

Sponsored Content by Taboola

The latest lifestyle and entertainment news and inspiration for how to live your best life - all from Good Morning America.
  • Contests
  • Terms of Use
  • Privacy Policy
  • Your Privacy Choices
  • Children’s Online Privacy Policy
  • Advertise with us
  • Your US State Privacy Rights
  • Interest-Based Ads
  • About Nielsen Measurement
  • Press
  • Feedback
  • Shop FAQs
  • ABC News
  • ABC
  • All Videos
  • All Topics
  • Sitemap
  • Recalls and Product Safety Alerts

© 2026 ABC News
  • Privacy Policy— 
  • Your US State Privacy Rights— 
  • Children's Online Privacy Policy— 
  • Interest-Based Ads— 
  • Terms of Use— 
  • Your Privacy Choices— 
  • Contact Us— 
  • Recalls and Product Safety Alerts— 

© 2026 ABC News