A Matchmaker Reveals What It's REALLY Like To Date An A-List Celeb

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Yes, we fantasize about being Mrs. Styles too. But could you actually handle the celeb world?

By Alessandra Conti

As a Matchmaker at Matching Up in Beverly Hills, one of the perks of my job is working with fabulous celebrity clientele who are looking for love. There are so many misconceptions about celebrities that I have learned throughout my years in LA (first off, they hate being called “celebrities” #oops).

Here's the thing: when it comes to dating, celebrities are not actually “just like us”. People in the public eye and the brave men and women dating them face unique challenges that I help them navigate.

As a Matchmaker and Date Coach, I am hired to help find single Bachelors and Bachelorettes love and figure out what has been keeping them from finding true love in the first place. Whether it is through Date Coaching a celeb-scorned Bachelorette or matching a celebrity himself, I've learned a thing or two along the way.

Most people are relentless. Well... kind of. 

Most people think that in LA the paparazzi are everywhere and that celebrities are constantly hounded by these blood-curdling vultures.  This is absolutely the case for the A-listers (my heart goes out to T-Swift when she just wants to do a makeup-free run to Whole Foods), but what most people dont know is that unless you are a Taylor, Angelina, Kimye or Britney, or have a major scandal going on, the paparazzi are rather easy to predict.

It's important to understand the general LA celebrity culture to understand the way they date and mate.  The best way I can describe the double standard comes from one of my favorite Real Housewives, Eileen Davidson: "Pay attention to me… don’t pay attention to me." An actor in a television series or a recording artist with a billboard topper from a few years ago needs to remain relevant.

Even with successful actors, there is still that ubiquitous hustle that they must continue in order to live up to the lifestyle that they have grown accustomed to. All because they starred in one blockbuster film does not necessarily mean that they are living the high life… or that they can maintain this lifestyle.

The nature of the entertainment industry is that the studios want to work with actors who are making the headlines, and it is important to understand that actors' publicists frequently go out of their way to literally make the headlines.

Exhibit A

A celebrity Bachelorette, we will call her "Jessica," had just been through an extremely public breakup with her famous ex-husband. Their relationship had been under constant scrutiny by the media for a number of reasons, so the fact that it was finally over was initially big news. Although making a name for herself, Jessica was primarily famous because of her husband.

It had been a few months since their breakup when I accidentally got a cc’d email from her manager. Since it was the first of its kind that I was receiving, I was shocked: the email was a tip off to the paparazzi saying that she would be going out to a Hollywood restaurant that night, what (and who) she would be wearing, and the name of the new "boyfriend" who would be accompanying her.

At first, I was a bit judgmental: tipping off the paparazzi is extremely looked down upon in LA, but then I realized that Jessica was creating a new headline because she was sick of living the story that was consistently being played out in the media.  Her breakup made headlines, and now her team was creating them.

Infidelity is the norm in Hollywood.  

As much as it pains me to say, the stereotypes are right on: Celebrities are not the most monogamous bunch. I cannot tell you how many stories I hear and see for myself on a daily basis of infidelity among celebs who are portrayed as pious in the media.

I was at a party at a "happily-coupled" actor's mansion in the Hills (who shall remain nameless… but believe me, you know who he is) and was not surprised when he ended up disappearing with one of my girlfriends who later slept over. I also later met two gorgeous models who also mysteriously pulled a Houdini for the majority of the party. One of my other friends used an upstairs bathroom and found them in a hot tub sipping champagne... it sounds so cliché that it almost pains me to write it.

Regardless, what we can take from this story is that this actor is a man who is painted as a family-man in the press.

A bad reputation is hard to shake.

I worked with one infamous client who was actually a total sweetheart. The media got her all wrong, and she is really just a sweet girl from a small town who got caught up in a whole lot of drama that was then plastered on every tabloid known to Ralph's.

Working with a matchmaker was a great idea, because I was able to give the bachelors I was matching with her the real deal about who she really was. Most of the bachelors who were not in the industry were open to giving her a chance, but we faced a major road bump with a man who I, to this day, believe is her soul mate.

Her best match, a behind-the-scenes mogul, was initially open to meeting her. He knew she didn't have the best rep, but was willing to overlook it because he trusted my judgment. Sadly, he did his own little Google-stalk and was horrified of all of the bad press. Being seen with her could damage his image, something that he was not going to risk, even in the name of love.

Actual A-listers are super paranoid.

Most A-list celebs are paranoid, and for good reason. Even with a fully executed Confidentiality Agreement, it was like pulling teeth to get one of my client’s home address, the one not listed on Star Maps. Our company also plans all of the dates for our clients, and we always book the restaurant reservation under a pseudonym.

Some star clients don't mind coming into my office in Beverly Hills; it is right by Sprinkles cupcakes #mydailystruggle. Others prefer that I go to their homes for meetings. I absolutely love this part of the job. I have been lucky enough to visit some of the most beautiful homes in Los Angeles; from Infinity pools overlooking the Hollywood Hills to entirely glass floors that peek into the full-scale wine cellar in the basement #casual, I have pretty much seen it all, and it really never gets old.

Do I love matchmaking celebrities? Absolutely.  But it is always wonderful to come back down from the Hills and work with my other bachelors and bachelorettes who are just looking for love, minus the paparazzi.

Want Alessandra to be your matchmaker? Visit www.MatchingUpLA.com for more!



This article was originally published at Guest of a Guest. Reprinted with permission from the author.


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