Chelsea lives in Pacific Beach and handles marketing for MarineMax San Diego, a prominent yacht dealer. Raymond lives in Golden Hill and manages Cusp, the restaurant atop Hotel La Jolla.
The two met for the first time half-an-hour ago and are now in an Epic limo headed to the San Diego Harbor, where they’ll leave dry land in a speedboat for today’s wakeboarding blind date.
Before they arrive to get fitted for wet suits and life jackets at Seaforth Boat Rentals behind the San Diego Marriott, let’s review the pre-date interviews.
PacificSD: What do you do for fun?
CHELSEA: Beach activities, hanging out with friends and rapping. The usual.
RAYMOND: Snowboard, play golf, volunteer. I like to dine out and have fun when I’m not working. I see people having fun at my restaurant every day. I like to have fun sometimes, too.
What are you best at?
CHELSEA: Dropping it low.
RAYMOND: Social interaction.
What do you suck at?
CHELSEA: Remembering people’s names. Someone could introduce themself to me, and then, five seconds later... poof! It’s gone.
RAYMOND: I suck at sucking. I haven’t found anything in particular that I’m awful at.
What are you looking for in a date, physically and/or otherwise?
CHELSEA: Someone who is adventurous, confident and has a good sense of humor. Physically, tall, dark and handsome. I have a thing for arms and a nice smile.
RAYMOND: Someone to have fun, laugh and smile with, just enjoy the moment together as best we can.
Describe your special brand of sex appeal in five words or less.
CHELSEA: Flirty eyes.
RAYMOND: “Have you ever modeled before?”
Rate yourself on a scale from 1 to 10 for looks.
How about for personality?
What’s your biggest fear?
CHELSEA: Sharks. I was forced to watch Shark Week once - worst hour of my life.
RAYMOND: Complacency. I never want to ask myself, “What if?”
What traits could your date exhibit that would be complete deal-breakers?
CHELSEA: The three Cs: clingy, cocky and creepy.
RAYMOND: Cankles, lacking a sense of humor, and saying “like” in every sentence.
How many people have you slept with?
CHELSEA: Saving myself for marriage.
RAYMOND: I don’t think that’s a fair question.
Fill in the blanks: I want my date to be “blank” and “blank.”
CHELSEA: Fun and Spontaneous.
RAYMOND: Spontaneous and funny.
Will the night end with a kiss, something more or something less?
CHELSEA: I don’t normally kiss on a first date, but I’ll keep an open mind.
RAYMOND: You know, I have ended plenty of dates without one - my choice, of course - and plenty with them. We’ll have to see how we connect.
What’s the most important thing in the world?
RAYMOND: Being happy and having a good time.
The daters arrive at the waterfront, toast shots of tequila in the limo and then head to the dock to get suited up.
The Naked Truth
The wetsuits (and more) come off
Their butts now in gear, Chelsea and Raymond are drinking beers astern as the boat cruises south to calmer waters sheltered by the Coronado panhandle. They sit close and laugh while ro-sham-bo-ing to see who will ride first.
Raymond’s rock crushes Chelsea’s scissors, and, in a surprise move (seeing as how the water is a chilly 66 degrees), Chelsea peels off her wetsuit and dives in. When the captain drags the pull-rope into position, she gives the thumbs-up, and he guns the engine.
Splash! Orange flag, U-turn, rope reset.
After a second false start, Chelsea stands upright on the charmed third, dashing Raymond’s hopes for a pressure-free ride. It’s clear she has done this before as she cuts back and forth across the wake. She’s smiling wide and shivering as she climbs back into the boat.
Unwilling to be shown up, Raymond strips to his board shorts, jumps in and gives the thumbs-up. The eight-cylinder Chevy engine torques, and he’s up. It isn’t long before he’s carving outside the wake and even attempting
jumps, “attempting” being they key word - he lands, just not on his feet.
When Raymond has had his fill of harbor face-plants, the captain drops an inner tube into the water. It’s too small for a side-by-side ride, so Chelsea climbs onto Raymond’s back, clinging to his shoulders as the boat picks up speed.
It’s an intimate experience if not a romantic one. As it turns out, Raymond’s shorts don’t grip as well as Chelsea does, and he’s holding them above his head as the boat circles back to pick up the pieces.
[Editor’s note: a naked dater before sunset is a PacificSD blind date first.]
By car, the trip from Coronado to C Level restaurant on Harbor Island takes 20 minutes, give or take. By fast little boat, however, it takes about five minutes. The harbor wind is chilly at this speed, especially for the wet blind daters, who’ve moved to the bow to warm up in the sun, seeming already to have warmed up to each other.
The limo meets Chelsea and Raymond at the marina next to C Level, where they grab their bags to get spiffed up for a fabulous meal “with views to dine for.” At a waterfront table with a view of the skyline, they enjoy a few of chef Deborah Scott’s select appetizers and cocktails before being split for mid-date debriefings.
PacificSD: How’s it going so far?
CHELSEA: It’s good. I’ve had a great time since I stepped into the limo.
RAYMOND: It’s good. She’s definitely cool. Good smile, fun. She’s maybe a little bit shy, but she’s definitely talkative.
What were your first impressions?
CHELSEA: Nice smile. First off, I noticed the tattoos, which I like, so that worked out nicely. The conversation flowed really nice.
RAYMOND: Definitely the right hair color, beautiful eyes. She seemed like she was down for fun. It’s a good start.
Is this the type of person you’d normally date?
CHELSEA: I wouldn’t say I have a type, but connection-wise, as far as talking, definitely someone I could consider.
RAYMOND: Considering I don’t normally date, I probably don’t have a good answer for that. At this point in time, I’m pretty much just looking for someone who’s fun. She’s probably younger than I expected, but she doesn’t seem too young.
How was wakeboarding?
CHELSEA: Fun. I was telling him actually that I was crossing my fingers the entire week that it would be wakeboarding.
RAYMOND: It was cool. She got up pretty good. I felt like I had a little bit of work to live up to. I was kind of thinking, “I can’t eat shit the first time trying to get up.”
What’s the most attractive thing your date has done so far?
CHELSEA: The fact that he was a gentleman, and helping me in and out of the boat. He was always very attentive, which I look for in a guy.
RAYMOND: Watching her suck crab meat out of a crab leg. And the way she bit the green bean. I was pretty sexually enthralled. It was a fun moment.
What would your parents say?
CHELSEA: They’d make a comment about the tattoos. I think they’d like him.
RAYMOND: I don’t know. I’ve never brought a girl home. My mom would think she’s cool.
Rate your date on a scale from one to 10 for looks.
How about for personality?
Do you want to kiss your date now?
CHELSEA: Too soon to tell.
RAYMOND: I’m more akin to saying yes than no.
Does your date want to kiss you?
CHELSEA: I mean, who wouldn’t?
RAYMOND: Not sure.
Seaforth Boat Rentals
A Dish Out of Water
Still wet behind the ears, the daters are ready for lunch
After the mid-date debriefings, the magazine crew finally leaves Chelsea and Raymond alone to enjoy the rest of their date away from the camera. The next morning, we call to find out what we missed.
PacificSD: How was C Level?
CHELSEA: I had a great time. I kind of felt like he was talking a little too much instead of maybe asking some questions. It was pretty funny, I was getting a lot of feedback when you took Ray on his mid-date interview. The table next to me was asking me all about it and giving their opinions. I think I would’ve liked a little more dialog.
RAYMOND: It was nice. We changed in the bathroom when we got there, which was interesting. We definitely got surprised with some good stuff to start off lunch.
What did the people at the table next to you say?
CHELSEA: They just had an opinion about everything. They were apparently listening to our entire conversation. Their comments were mostly that he was talking too much, and I needed to be talking more.
What did you have to eat and drink?
CHELSEA: Not really sure what the drink was, but it was delicious. They brought out the appetizer that was a tuna-poke-type thing that was amazing. And I’ve heard amazing things about the burger, so of course I had to order that. It was amazing.
RAYMOND: We had this crab, tuna, avocado stack to start, then the Kobe filet burger and the skirt steak salad to eat. To drink, we had a seafood bloody Mary, the Scallywag, and another grape and vodka cocktail. We finished lunch with some Don Julio 1942 tequila.
What happened after the magazine crew left?
CHELSEA: We decided to call it a day. We exchanged numbers and dropped him off first. When we got to his place, we just hugged it out.
RAYMOND: We were planning on going home, showering and meeting up later that night, but I had to get up at 6:30 for a big Mother’s Day brunch at work, so we decided it might be better to just meet up another time.
Was there a kiss or romantic exchange?
CHELSEA: Just a hug.
RAYMOND: There was not. It was a little weird when the driver stopped and then put up the privacy curtain.
What two things would you change about your date to make the person a better fit for you?
CHELSEA: Maybe slow down a little bit, take a breather and have a bit more of a conversation, I guess.
RAYMOND: Maybe, if there was one thing I would say, it would be to not be as proper. Being proper is a great asset, but not all the time. Maybe a little more touchy-feely, if I had to choose something else.
What’s the funniest thing that happened during the date?
CHELSEA: The guy that drove our boat, I work with him and see him on a regular basis. So that was kind of funny, to be, “Oh, hey. I know you.”
RAYMOND: I lost my shorts in the water. Yep, everything came off.
What was the best part of the date?
CHELSEA: Just having a nice conversation with each other when we felt a little more comfortable, and being able to open up.
RAYMOND: Hanging out with someone that I was actually interested in what they had to say. She is a really nice girl and has her shit together, or so it seemed.
Will there be a second date?
CHELSEA: I would like to see him again, but I’m old-fashioned. I would like to go on a proper date.
RAYMOND: I think so. We’ve been in contact since the date, and it seems like there is a mutual interest in hanging out again.
AFTERMATCH: Perhaps a second date would go swimmingly for these two. Chelsea thought Ray was a gentleman. He liked “watching her suck crab meat out of a crab leg.” She wants a proper date. He thinks she’s too proper. Is that ironic? If not, maybe this is: the date took place on a boat, and a second dinghy appeared... but then Ray put his shorts back on.
880 Harbor Island Dr., Harbor Island
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