She wants to keep her matchmaking style fresh for these modern times.

And what's fresher than two super young millionaires.

Bill is a Silicon Valley type, who hasn't had much luck with the ladies.

He's a ginger, but Patti is feeling his "Eric Stotlz" vibe

Destin's making sure to TiVo a few things before checking out the other millionaire.

Skylar's a bit of a playboy, but he's looking to settle down.

Can Patti find him his non-crazy Britney Spears type.

Skylar runs Brentwood -- but he's running it alone.

The nightlife impresario is looking for a girl to work things out with.

And possibly to share headbands with.

He's got a sweet ride.

When it runs. . .

Bill's looking a little too all-business with Patti.

He can't tear himself away from the computer screen.

Even when precious puppies try and distract him.

Patti is not amused by the amount of technology this kid's packing.

You're smiling now kid, but you'll never see your iPad again.

Skylar on the other hand kicks it old-school.

Note the hand chair -- classic bachelor pad.

Skylar's got a little secret -- he's never had a girlfriend.

In order to up Bill's game, Patti calls in the big guns -- Jenny McCarthy.

Patti wants Jenny to teach this kid everything. . . seriously, everything.

Jenny has a thing for nerds, and Bill has a thing for Jenny, as his heart-rate shows.

The boy just wants to be guided. Help him Patti.

Hmm, she'll be the perfect tester.

If there's cleavage, Patti will find it.

Patti finds a blonde that could be perfect for Skylar.

Festive cocktails and minimal dress required

Careful ladies, it's a two-drink maximum.

Skylar asks Bill to be his wing man.

Offer accepted.

The literal dating pool.

The girls lock eyes with their prey.

Skylar likes what he sees.

And what he sees is hot chicks in bikinis.

More hot chicks in bikinis!

Additional hot chicks in bikinis!!!

Patti is not a Dougie fan.

Teach them how to Dougie Bill. Teach them how to Dougie.

Patti wants to know who caught Sky's eye.

Notice how far her legs are away from him. Not looking good buddy.

Bill does his best to not discuss his job.

Much better.

Bill and Tracey seem to be hitting it off.

And Tracey's not too bummed either.

Jenn is thrilled to be the choice!

Already going in for the kill. Easy tiger.

Looks like he's cheating

Pre-date hugs.

And give him an excuse to get close to Jenn.

Skylar thinks hot yoga will make things hot.

Even a gingy can find love!

She's loving his nerd convo and self-effacing jokes. Jenny McCarthy taught him well.

But his date doesn't seem too bothered.

Skylar admits he's never had a gf.

She doesn't look exactly killed.