15 Ways Dating A Rich Guy Can Get Awkward

Let’s just say what’s on everybody’s mind: dating someone with a lot of money is kind of amazing. We’re not saying you look for someone with money, but when you happen to fall for someone who has money, a lot of stresses that come with most relationships just aren’t there. But then again, dating someone much wealthier than you comes with its own challenges.

Your friends work where he takes you out

That super expensive restaurant where you used to sit at the bar while your friends who worked there snuck you free drinks—yeah, now you’re sitting in the actual dining area and ordering champagne. And your friend is taking your order.

People wonder if you’re the help

When you park your beat up car amongst all the cars at his condominium complex that cost more than you make in two years, people wonder if you’re the nanny or house keeper or there to pick up donations.

His assistant makes more than you

And you’ve sort of considered applying for the position.

He can never find parking at your place

Because your tiny apartment came with one or zero parking spots, he has to circle for at least a half hour every time he comes to visit you in your overcrowded neighborhood.

He has to deal with your roommate

For the first time in years, he has to mind another person roaming around the place he is sleeping. At his enormous place, he can walk around naked if he pleases.

You have the generic label food

He asks where your Perrier is and you sheepishly point at the strange-looking canned Perrier copycats you bought at the 99 Cent Store.

He ends up paying for your friends…a lot

Either because they get too drunk and “miscalculate” how much to throw down on the giant bill, or because he invited them to somewhere super expensive, your guy is generally the one picking up the tab.

Double dates are really tough

Your friends’ boyfriends can’t afford to go to the places your guy suggests for double dates. Or you go to the places your friends can afford and the entire time you’re thinking about how your guy would probably prefer for the two of you to be elsewhere.

Sometimes, you feel like you don’t have the right wardrobe

He wants to go to really nice events and you do not have many floor length gowns to choose from. While you feel that your wardrobe is pretty decent, the pressure to impress is ever-present.

You generally fly coach, but he prefers first class

Planning romantic vacations get pretty interesting when you two have to catch a plane to reach your destination. Will you upgrade to first class or will he settle for coach? Decisions, decisions.

You can’t afford to drop everything and travel with him

He randomly booked a trip for the two of you on an exotic island at a five star resort, but your job doesn’t allow you to schedule days off. What ever will you do?

You sometimes wonder why you’re still working

There is that awkward question lingering in both of your heads that asks, “Why are you even still working? He could cover your rent and it wouldn’t even put a dent in his bank account.” But then your sanity kicks in and you realize that if things don’t work out with you two, you’d be broke, unemployed and possibly homeless.

You cut coupons

You’re still very much in the mindset of shopping around for a better price, asking for discounts and looking up coupons; however, it feels awkward when you do that in front of him.

Dinner with your parents is usually his treat

He pays for your parents because, realistically, picking up the bill won’t put a dent in his pockets and of course, he wants to make a good impression.