Not all celebrities are comfortable with the idea of dating to begin with, nonetheless paying people to date them. Some of the most worthwhile relationships are those that were made because someone took a leap of faith and didn't gawk at being rejected in the process.
While it may not sound likely that a celebrity would have a hard time paying someone to date them, the scenario is perhaps more common than one might assume. First of all, many cases of celebrities paying people to date them involve fellow celebrities.
Actors, singers, sports stars and celebrities from any background you can imagine have been reinventing their dating lives with making money work for, not against them. Perhaps one of the main reasons a celebrity would pay someone to date them would be to maintain honesty and ensure fun in the relationship for both parties.
One may think that dating a celebrity is impossible or not worth the risk. Well, it might be worth pointing out that a date doesn't require marriage, but also doesn't exclude it, either. It's totally possible for a married celebrity to pay their husband or wife to date them, even if said spouse is a celebrity as well!
Many celebrities don't have much time for dating. When there are paparazzi following your every move, the ability to maintain a normal dating life can be a challenge. In this list, we'll take a look at 15 cases of celebrities who have been exposed spending money on dates.
16 Hugh Hefner
Recently departed Playboy owner Hugh Hefner has had photos of his dates displayed in everything from magazines to prime-time specials. Ultimate sugar daddy and guru to pick-up artists everywhere, Hugh Hefner knew dating. In this photo, we see Holly Madison and Hugh Hefner at a table that is covered in plates and drinks of all types. Apparently in addition to the lavish dates that Hugh Hefner paid for with Holly Madison, he was also willing to front her $3 million to stay with him at the Playboy Mansion. While the offer may have been tempting, the E! Network star decided to pack her bags and take a chance on her own; no more dates on the fly with the one and only Hugh Hefner! Without an actual copy of the bill from this dinner date we can't be 100% sure that he paid the world's most notable adult film star's tab, but if we're talking about Hugh Hefner, there's a good chance that was the case!
15 Chris Brown
Multitalented entertainer Chris Brown has had his fair share of dates. Some may not have even heard about Chris Brown before the headline-making date disaster with fellow megastar Rihanna in 2009. Since the notorious breakup with Rihanna, Chris Brown has continued dating despite being highly scrutinized and serving 5 years on probation for domestic violence. Celebrities don't have to pay for dates considering the sheer number of fans who'd die to be in the same room with them. In the case of celebrities with a huge female following like Chris Brown, dates must come with a price and in the above photo there's more than just romance, but actual dollars on the table. While we don't know which restaurant this image was taken in, none other than Karrueche Tran was the person who had the "Beautiful People" paying for the scrumptious date.
14 Justin Timberlake
Like in our previous entries, this photo is evidence of a bonafide date with a celebrity, and not just for a coffee. Justin Timberlake has paid for more than what meets the eye in this photo, and that's assuming that he didn't cover the tab of fellow celebrity Jessica Biel. These two are enjoying a round of refreshments at none other than the US Open, which took place in New York City in September of this year. While a quick glance of the photo might give the impression of two people at any normal casual diner around the country, a closer look reveals that this special moment was definitely paid for by the singer of 2017's arguably hottest male vocal track, "Can't Stop The Feeling." There's no doubt that no matter how you look at it, a date with JT would be worth millions, but in 2017, the price for such a rendezvous might be at an all-time high. Having the money that JT has, there's little doubt that he'd show his girl anything less than a venue like the US Open and all the perks that money could buy!
13 Jennifer Lopez
Jennifer Lopez and Alex Rodriguez may have started a new trend with their combining their birthday celebrations into one mega-date. Included in this date extravaganza was dinner at Miami's Prime 112 restaurant, tons of birthday cake, and dancing. The pair who have been nicknamed 'J-Rod' made the practice of dropping tons of cash for dates popular since they both had the motive and the money to cover one another's wishes. If their birthday's hadn't fallen in the same month, perhaps the date weekend wouldn't have been nearly as memorable. Unlike most cases where celebrities pay people to date them, this dynamic made for not only more spending but more time as well. Photos of J-Rod's 2017 birthday date weekend were posted by both Jennifer Lopez and Alex Rodriguez on their own Instagram accounts, and they definitely don't disappoint! So here's to J-Rod for making it clear that celebrities don't just pay for their dates with other celebrities, but can also mutually pay for lavish dates!
12 Miles Teller
Through the years celebrities have had to balance the limelight with their dating lives. In this photo, actor Miles Teller and his girlfriend Keleigh Sperry are seen not only spending time together on a date, but clearly have just been on a shopping spree. The recently engaged couple looked happy shopping during their time in the trendy SoHo district just before their engagement earlier this year. While it's hard to prove whether this photo isn't a result of going dutch, the gift bag is a possible tip that despite traditional expectations of the newly announced groom Miles Teller (holding the nondescript gift bag) paid for whatever's inside. This uptown shopping spree is just one example of this couple's extravagant romantic outings which have also included African safari's, shopping trips, and a myriad of other pre-wedding dates. Ah, the joy of being an engaged celebrity couple.
11 Tiger Woods
Golf legend Tiger Woods has been back in the dating scene since breaking up with wife Elin Nordegren in 2010. Since the tumultuous breakup Tiger Woods has managed to remain active in the dating scene as boyfriend to 33-year-old Kristen Smith. After a DUI arrest Tiger Woods called Kristen Smith to inform her of the news. When Kristen Smith heard of the arrest, she went into a panic and subsequently spent over $4,500 at a Neiman Marcus location. The UK Sun didn't say whether or not Tiger Woods knew that his girlfriend was at a Dallas, Texas shopping boutique at the time of his arrest, but if so, then maybe it's not just an example of a celeb paying for a date, but a remote date, at that!
10 Matt Damon
Matt Damon officially left the singles market in 2005 upon his marriage to wife Luciana Barroso. Since tying the knot the couple have enjoyed numerous extravagant outings together. If there is smoke there is fire, and with not too much digging there's always a way to discover evidence of celebrity date buying. In the case of Matt Damon and Luciana Barroso, one only need to look back to June of this year for juicy date details. On June 24th, the couple was spotted eating at a Los Angeles restaurant. Just this month on October 4th, the couple were seen enjoying a Coldplay concert in Pasadena, California. A few days later, the couple were spotted at the Rose Bowl with fellow celebs Demi Moore and Mary J. Blige. In the last 2 examples of Matt Damon and Luciana Barroso's dates listed above, we might venture a guess that it was actually a multiple day date. One thing's for sure; this celebrity couple is paying for dates and in no small fashion!
9 Michael Jordan
Michael Jordan is now reportedly one of the few celebrities who have spent lavish amounts on dates. This celeb spread the drinks around the table with new wife Yvette Prieto. With having a table that couldn't be more packed with refreshments, there's little doubt that whoever's in the photo is either paying for a date or keen to the experience of such! Making a stronger case for this is the fact that the Hornets owner and National Basketball League Hall of Famer marked his 2013 wedding with an over-the-top accommodation that suggests he knows the ins-and-outs of paying for extremely extravagant dates. All kidding aside, there is certainly one thing for sure here; Michael Jordan and wife Yvette Prieto are on a journey that has been fortunate enough to now include a new baby!
8 Charlie Sheen
Charlie Sheen has definite reason to make this list. According to some reports, the notable celebrity of both TV and film fame has spent more than a million dollars paying for dates. Some of the most memorable celebrity romances of recent years have involved Charlie Sheen, most recently with adult film star Julia 'Jools' Stambler who has not been bashful since learning of Charlie Sheen's HIV status. While it's clear that Charlie Sheen has dealt with plenty of dating scenarios in his life, he makes a great example of a celebrity who has found success in dating through paying not just his way, but his partners-in-crime as well. Who knows, maybe dating a celebrity isn't impossible after all.
7 Patrick Dempsey
Patrick Dempsey and wife Jillian Fink make our list due to being one of the relatively few cases of a celeb marrying a non-celeb. Dates between a non-celeb and a famous actor such as Patrick Dempsey can be speculated about for many reasons. Perhaps it's unusual for the non-celeb to experience the limelight that comes with dating a celeb. No matter how the dynamic may seem to differ in the case of celebs who date non-celebs, the dates are lavish nonetheless. Since getting married in 1999, this couple has proven that anyone wanting a chance of love with a famous movie star has a shot, if there's chemistry involved. This couple may prove that when a celebrity pays someone to date them, the result may be the same as if they didn't spend a dime.
6 Jerry Seinfeld
With more than half a billion dollars to spend, Jerry Seinfeld has more than enough means to keep anyone happy on a date. Not many celebrities can boast such a high net worth. Some figure that sums of more than a few dollars can cheapen romantic moments, especially if those times are all too far and few between. Philanthropist Jessica Seinfeld has an endless variety of options when going out on dates with her former Seinfeld star and husband. Can you even imagine the kind of decisions you could ponder while making plans for a dream date with one of the most famous and wealthy celebrities in the entire world? Paying for dates might be the role of Jessica Seinfeld, as the best way to enjoy a date with a partner who's able to cover any financial cost might be to do the spending. Together, this power couple definitely make us melt green with envy.
T.I., the highly praised Southern musician who rapped into pop-culture the idea that "You Can Have Whatever You Like," is one who knows how to spend money on dates. Celebrity marriages can be tumultuous, especially when you're a top rap star with a reality show to boot. It's plausible that celebrities can more freely spend on dates since in a way their star-power is a form of payment (think celebrity endorsements), but a Southern gent celeb might have a head-start on how to really show a girl just what it means to be a gentleman. Since he became a popular fixture in pop culture, many girls and groupies have craved his attention, yet due to his marriage, they haven't been able to achieve anything more than a sweet fantasy with the rap legend, until now, that is. After officially divorcing from his ex-wife Tiny Harris just this year, he pulled out the champagne at no other venue than the Super Bowl with a mysterious beauty named Kristin Ingram. This may have not made Tiny Harris very happy! Apparently one of this paid celebrity dates' highlights was something that was shared on Instagram: '#champagneproblems' – most of us could only dream of such woes!
4 Patrick Stewart
Celebrity powerhouse Patrick Stewart has made some of the 2010's best action movies so far, and we're not just talking about any of the X-Men flicks. It may go without saying that having achieved tremendous success in both the film and television arenas makes for plenty of dough to lavish a date with. Well if you don't think that only the best dates that money can buy are being shared between this A-lister and his wife Sunny Ozell, think again. Just this year the couple have shown up together at two of the world's hottest dating crown-jewels: the Hamptons and Berlin! In the Hamptons, Patrick Stewart showed his wife the kind of date that only the setting for Revenge could provide; likely inclusive of the best seafood and gorgeous ocean views. In the city of Berlin, Germany, the knighted actor likely waived his royal rights and paid his own tab at some of the most desirable locals to take a spouse in the known world.
3 Demi Moore
Demi Moore has not given up on love since her divorce with fellow celebrity Ashton Kutcher in 2013. Demi Moore has taken her love life by the horns since splitting from the seemingly fairytale-perfect relationship with the Two And A Half Men star. Some stars would have totally given up on dating after such a public and gut-wrenching breakup, but this former Charlie's Angels star has proven to manage quite well with her incredible amount of money and all that goes with it. When coupled with money, being famous is a recipe for dipping back into the dating pool with a serious vengeance. In the above photo, Demi Moore lays under an umbrella on a plush beach with none other than her date, 27-year-old hunk Sean Friday, who is adoringly leaning over her, perhaps to check out the waves in the date's sublime background. Sometimes a woman's got to take control, and all we can say is, more sunblock with those lobsters, please!
2 Samantha Ronson
Dating one of the most treasured actors of a generation never comes without demonstrating you that you have the ability to support them with diamonds and cold hard cash. As a top New York City DJ, Samantha Ronson made sure that Lindsay Lohan wasn't without the power of choice during the dates scene above from the early 2010's. All too many forget that one of the most desirable aspects of a shopping date is the gift of having the freedom to choose whatever you like. Since the infamous duo was officially dating at the time, these rare images of Samantha Ronson with a wad of cash in-hand for (presumably) girlfriend LiLo to spend are perfect examples of a celebrity who was caught paying for dates with the gorgeous and the famous. Thankfully, it's not just normal people who celebrities that know how to pay for a date have to choose from when looking to enjoy some of the best times of their lives.
1 Meghan Trainor
Meghan Trainor and Daryl Sabara are seen holding hands after making purchases at Sur La Table over the 4th of July weekend. The singer of "Dear Future Husband" has a somewhat mysterious look in this image since her eyes are hidden beneath flash-coated aviators. However, her beau Daryl Sabara is no easier to read, given his face is turned to the side. Since the pair started dating in July of 2016 there have no doubt been plenty of opportunities to decide who pays for what and when. Hopefully we can see some pictures of whatever was purchased from Sur La Table on Instagram soon!