Photos by Rick Nocon | Matchmaker: Jessica Pelligra
What are the odds of finding love on a first date? As luck would have it, the answer may soon be revealed. Blind daters Jolie and Trey met about an hour ago in the Epic Limo that's about to drop them off at Sycuan Casino for a high-stakes evening of excitement and entertainment. Before they arrive for the big night, let's review their pre-date interviews.
PacificSD: Where are you from and where do you live now?
JOLIE: I am from San Diego, and I currently live in Encinitas.
TREY: Originally from Arizona, lived in San Diego for two years.
What do you do for a living?
JOLIE: I am an intuitive business coach. My signature course, Prosperity Possy, is an eight-week business accelerator to help millennial women start soul-aligned businesses from scratch - "Possy" with a "Y" to remind women that pleasure creates prosperity. I am also a writer. My book, Empowered, Sexy and Free, was published in 2015 and is an Amazon best seller. And my blog is on JolieDawn.com.
TREY: Just started my MBA at USD. I run a vacation rental in Rosarito for extra cash, building a business in sustainable real estate and helping the impoverished.
What do you do for fun?
JOLIE: I am a total beach lover. I absolutely love swimming in the ocean, surfing and hanging with friends on the beach.
TREY: The basics include everything that has to do with outdoors: hiking, camping, fishing, surfing, etc. All about good dive bars with friends and causing a bit of trouble on the weekends. Love photography
and other creative activities. A good laugh is of utmost importance.
What are you looking for in a date, physically and/or otherwise?
JOLIE: I'm looking for a guy who knows who he is, a guy who is curious about me and is able to meet me at the bigness that I play in life.
TREY: Seventy percent comes down to brains and personality, 30 percent physical attraction. A good combo of both, of course, is a win-win.
Describe your special brand of sex appeal in five words or less.
JOLIE: Spiritually connected, takes great care of his body, able to hold a five-minute eye-contact gaze, beautiful smile, eyes that tell a story.
TREY: Intellectually smoking-hot mermaid.
Rate yourself on a scale from one to 10 for looks.
Rate yourself on a scale from one to 10 for personality.
What's your biggest fear?
JOLIE: Laying on my deathbed, talking about what I wish I would have done in life.
TREY: Hippopotomonstroses-quippedaliophobia, the fear of long words.
What traits could your date exhibit that would be deal-breakers?
JOLIE: Insecurity, hesitation, negativity, complaining and disrespectful.
TREY: Armpit hair.
How many people have you slept with?
JOLIE: I'm a huge fan of sleepovers and cuddles. I have my girlfriends stay over on the regular, so I would say hundreds of people I've slept with.
TREY: Greater than 40, less than 100? Never counted.
Fill in the blanks: I want my blind date to be "blank" and "blank."
JOLIE: I want my date to be 100 percent himself and to make me laugh.
TREY: Under 40 and a female.
What's the most important thing in the world?
JOLIE: The most important thing in the world is to remember that life is temporary; we are spiritual beings having a human experience; and that anything is possible while you're here on this crazy rock we call Planet Earth.
TREY: Well, Bob, if I may, we need to figure out how to not destroy this Earth into oblivion before we destroy this Earth into oblivion.
As their limo pulls up to the valet, the daters hop out, and then head inside the casino.
Hip Hop Hooray
Time to get down with O.P.P.
Hip Hop Hooray
Drinks to break the ice are usually a safe bet, so Jolie and Trey head to Wachena, Sycuan's snazzier dining option. Things appear to be going well as they talk and laugh over cocktails and apps.
About 30 minutes later, they leave the restaurant and head to Live & Up Close, the casino's intimate concert hall. Tonight is the San Diego '90s Jam, featuring a roster of headliners. Before the show begins, the couple heads backstage to meet the bands - Naughty by Nature, All 4 One and Coolio. (En Vogue will also perform but didn't participate in the meet 'n' greet).
As the lights go down, the daters find themselves in gangsta's paradise (to quote a Coolio song). They dance to hit after '90s hit (including All 4 One's "I Swear," and Naughty by Nature's "O.P.P."), getting on-stage props from the performers they met earlier. The place is bumpin'.
After the concert, the couple heads to Game Day Sports Bar for a quick break. Before trying their luck at blackjack, they're split for mid-date debriefings.
PacificSD: How's it going so far?
JOLIE: This date is ridiculously fun. Trey and I had an instant connection, and I'm really loving getting to know him in this not-so-conventional way.
TREY: Quite well, thanks.
What were your first impressions?
JOLIE: My first impression of Trey was, "OMG, he's way hot!" My heart was happy. Tall, hipster, beautiful smile - yes, please.
TREY: I was kinda blown away by her looks. She held herself well.
Is this the type of person you'd normally date?
JOLIE: He's not normally the [type of] person I date. I'm typically attracted to older guys, at least 10 years on me, solely because of maturity, but Trey is surprisingly mature for his age.
TREY: Absolutely. She has both the looks and the brains.
What do you think about the way she dressed?
JOLIE: I loved the way he was dressed. Sexy hipster.
TREY: She was stunning.
What do you think of Sycuan?
JOLIE: Sycuan Casino is awesome. I really love the venue and would love to come back for another concert.
TREY: I've never been to a casino around San Diego but I'm pretty impressed with Sycuan. Awesome staff, venue and casino.
How was Wachena?
JOLIE: I'm typically not a casino person, but Sycuan has a fun vibe.
TREY: The food was great. The restaurant had a very chilled atmosphere.
How was meeting the bands before the show?
JOLIE: Pretty awkward.
TREY: Awesome. I felt like I was back in high school, bumping in my car with subwoofers that took up the whole trunk.
Describe the atmosphere at the concert?
JOLIE: Concert atmosphere was rad, really intimate and comfortable.
TREY: I really enjoyed the concert. Even though a '90s rap concert was in a seated concert hall, everyone was out of their seats getting down.
What's your date's most attractive quality?
JOLIE: His ability to crack me up. I don't think I've stopped laughing since I met him. I find him hilarious. And I loved hearing about the entrepreneurial passion project he's working on in Mexico - a fellow achiever.
TREY: I was pretty attracted to how she was getting down on the concert floor. The girl's got moves. She was all-around stunning. She also has a great ass.
How about a least attractive quality?
JOLIE: His least-attractive quality is the fact that he's so close to my age.
TREY: If I want to see her again, I probably shouldn't answer this question.
Rate your date on a scale from one to 10 for looks.
JOLIE: Trey is a 10 on looks for sure.
TREY: I'll give her a 9.5. Nobody's perfect.
How about for personality?
TREY: Again, a 9.5.
Do you want to kiss your date right now?
JOLIE: I totally want to kiss Trey right now, and, as they keep bringing us tequila, that desire becomes very real.
TREY: Hell, yeah!
Does your date want to kiss you?
JOLIE: Yes, he totally wants it.
TREY: I just sent her a text, asking. No response yet. Not a good sign.
Anything else you want to add?
JOLIE: At the first moment [we had] to chat, we immediately started talking about the similarities of our pasts. He lost his dad just three months ago, and I lost my dad six years ago. It's a super-fresh loss for him, and it doesn't freak me out at all. I know exactly what it feels like to be in that space so I could ask questions and support him in a way that most people just don't know how to. I absolutely love who Trey was for his family. It reminds me a lot of the way I show up.
TREY: Save the whales.
5469 Casino Way, El Cajon
It's in the Cards
It's in the Cards
After the mid-date break, Jolie and Trey head to the card tables, each armed with $100 in gambling money courtesy of Sycuan. As they begin playing blackjack, he gives her pointers, helping her decide when to hit and when to stay. Once they've had a chance to place a few bets, the magazine crew finally leaves them alone to enjoy the rest of their evening away from the camera. The next morning, we call to see what we missed.
PacificSD: How was blackjack?
JOLIE: Blackjack was a blast. Trey was teaching me how to play, and we were cracking up the whole time. He and I made a deal that we would bet high and, whoever won, we would split it. I tripled my money, and he wouldn't let me split it with him.
TREY: Blackjack was fun, but I lost my ass. I was out in about five minutes, while Jolie doubled her money without knowing how to play the game.
What did you do for the rest of the evening after the magazine crew left?
JOLIE: We both were wanting some nature after being indoors in the casino all night, so we had the driver take us to the beach. The chemistry was undeniable, and we did not want the night to end early.
TREY: We had the limo driver take us to the beach after the concert. Being inside all night made us want to be in some nice outside setting where we could talk.
When did you get home?
JOLIE: We stayed at the beach for a few hours. It was a surprisingly warm summer night with a mostly full moon, and we did not want to leave. The conversation was flowing so easily, and it felt like we had years of life to catch up on. I got back to my place after 1 a.m.
TREY: 12 a.m.? 1 a.m.?
Was there a kiss or romantic exchange?
JOLIE: There was an incredible romantic vibe. He was holding me so sweetly on the beach. I absolutely loved being in his energy. I felt like I had known him for a long time; it was so comfortable. We are going to explore our chemistry and connection on date Number Two.
TREY: We kept it tooootally platonic.
How and when did the date end?
JOLIE: After the beach, we took an Uber back to my place, he walked me to the door, and we held each other for a few minutes. Then he took the Uber to his place.
TREY: The date ended around 12:30. It was a nice ending where we both sat on the beach and talked about each other's lives. I got to learn a lot about her and the amazing work she does with helping women quit the jobs they hate and follow their dreams to entrepreneurship.
Fill in the blanks. I wish my date had a bigger "blank" and a smaller "blank."
JOLIE: Bigger range of dance moves, smaller concern about what he looked like dancing to En Vogue.
TREY: Wow, the amount of inappropriate things I can come up with.
What's the funniest thing that happened during the date?
JOLIE: Trey was cracking me up the entire night. The funniest thing was sitting in the front row, jamming to "Gangster's Paradise," feeling entirely un-gangster. It was where we really stopped trying to impress each other and just settled into the hilarity of the moment.
TREY: I would have to say when Coolio pointed to Jolie and called her out for being the whitest girl in the venue. That was a good laugh.
What was the best part of the date?
JOLIE: The best part of our date was our instant connection. I absolutely loved talking about our businesses together. I think it's super rad that he's starting a destination property in Baja, Mexico, to employ the homeless and create sustainable, luxury and communal travel. For-benefit businesses turn me on.
TREY: It's hard to say; all of it was great. The concert was fun, but I think the best part was being at the beach and talking. It was really the first time that we were alone and able to get to know each other.
Will there be a second date?
JOLIE: There will absolutely be a second date. He made me feel so honored and adored. Plus, I think we look totally adorable together.
TREY: Yeah, there will be a second date. We got along great and have a lot in common when it comes to our personal and professional lives.
What's one thing your date really should know before going on another date?
JOLIE: He should know that I am moving to Austin for the fall and have a ton of travel adventure and business expansion plans coming up in 2017, so I am not entirely available as a committed partner.
TREY: With someone else? With me? With who? Know about herself? Me? Another dude? No clue. I don't know what you're asking.
Anything you'd like to add?
JOLIE: I was so nervous before the date; I kept having to remind myself to breathe. As soon as we met, all of the nervousness left. I feel so incredibly blessed that Trey came into my life, especially so unconventionally. Maybe we have a story to tell the grandkids?
AFTERMATCH: Luckily for last night's blind daters, their experience lived up to Sycuan's slogan: Play. Win. Together. In the heart of San Diego. They played. She won. They had a blast together - and were close enough to the city to enjoy a romantic interlude on the beach. Gambling on whether these two would hit it off was a safe bet from the start, one that was confirmed at the mid-date break. She said, "I totally want to kiss Trey right now." He said, "She was all-around stunning. She also has a great ass."
The house always has the advantage, but Jolie and Trey got free dinner and front-row seats, and then left the casino with cash in their pockets. In this case, despite what may have happened on the beach, the second "P" in O.P.P. wasn't, as Naughty by Nature sings, "another way to call a cat a kitten" or a "five-letter word rhyming with 'cleanness' or 'meanness.' " It was pure "paradise.