Penguins hottie Jordan Staal is one of the most eligible bachelors in the NHL and Ashley A. is a two year veteran of the Washington Redskins Cheerleaders. 
Why it would work: They're young, they're blonde, they're (presumably) into sports and Washington D.C. is a mere four hour drive from Pittsburgh.
Why it wouldn't: Staal is a well-known party animal; if Ms. Ashley likes to keep it low-key and liquor-free, that could become a bone of contention.

Singer Nicki Minaj is an emerging superstars and the Wizards John Wall needs some superstar lessons. Wall has got potential, but the Wizards as a whole have no idea how to create a buzz.
Nicki Minaj courtside would create a buzz. 

With his career on the decline, golf legend Tiger Woods may be looking for some stability in his life after his much publicized divorce from Elin Nordegren. Enter Rebecca Grant.
Grant is an actress, model and sports enthusiast who began her television career as the on-air host for the Buffalo Bills NFL Show. In addition to her stints at ESPN and FoxSports, Grant has appeared in commercials for Budweiser, Coors and Keystone.
Why it would work: It doesn't seem like a wholesome blonde can keep Woods' attention. Grant is just the opposite; a seductive brunette with ample assets who may be wholesome, but you'd never know from looking at her.
Why it wouldn't: It's been established that Tiger has some minor issues with commitment and fidelity.

Orlando Magic forward Dwight Howard is a trash-talking NBA superstar who has a son with Royce Reed, a former team dancer who was a cast member of VH1's Basketball Wives. 
Arianny Celeste is a UFC Octagon girl and sometimes model who has appeared in Maxim, FHM, Sports Illustrated: Swimsuit Edition and, naturally, Playboy. 
Why it would work: He's a superrich, superbuff, superstar athlete and she's a superhot, supersexy, superstar ring girl who is looking for more than just a credit card.
Why it wouldn't: Howard seems to be a philanthropic family man with a home base in Florida. Celeste, who is also involved in charitable causes, seems to be a jet-setting model who might find it difficult to sit still for too long.

Green Bay Packers quarterback Aaron Rodgers loves hot blondes (Erin Andrews, Destiny Newton, Hillary Scott, Julie Henderson) and smoking' hot model Kate Upton likes flirting with football players (Rob Gronkowski).
Why it would work: Models and professional athletes are like peanut butter and jelly; they just go together. Plus you need to be a seriously confident human being to date a broad like Upton, and we all know Rodgers is confident (bordering on smug) these days.
Why it wouldn't: Well as desirable as the 28-year-old Super Bowl winning quarterback Aaron Rodgers is to the general female population, 19-year-old Victoria's Secret model Kate Upton just may be out of his league