Alyssa and Kyle don’t know it yet, but they’ve got quite a bit in common. They’re both entrepreneurs, they both make money by motivating people and they’ve both been avoiding the dating scene for the better part of two years.
But today, they’re stepping out of their comfort zones and trying a few new things to spice up their lives. First up is a paddleboarding session off Coronado’s coast, followed by dinner and drinks at an Italian eatery with a view in Imperial Beach.
Before the pair is whisked away from their respective homes by an EPIC limo, let’s review their pre-date interviews.
Where are you from and where do you live now?
ALYSSA: I’m from Rancho Palos Verdes and currently live in San Diego.
KYLE: Born in Canada, eh. Grew up in Lake Tahoe, and now I live in San Diego. Soon to be a full-time globe-trotter. Thailand is up first.
What do you do for a living?
ALYSSA: I’m an entrepreneur as the owner of Alyssa Rose Fitness.
KYLE: I believe in the 4-Hour Workweek, mini retirements every couple months and having money work for you. I help people create that lifestyle and bring their life to new heights through my brand/company, NewHeidts.
Why are you going on a blind date in PACIFIC?
ALYSSA: As someone who is constantly working on my business, sometimes the adventure and dating aspects of my life suffer a little, so I thought it would be fun and add something spontaneous to my life.
KYLE: I bumped into a girl, and after some small talk, she was like, “OMG, you have to meet my friend. She’s a matchmaker.” An hour later, I’m giving her my information, getting set up for this, and now I’m doing this interview. I’m in deep now and I can’t turn back.
What do you do for fun?
ALYSSA: I weight train, hike, I go shooting, hang out and play at the beach — anything athletic! I am a little bit of a tomboy. I also like shooting pictures and filming and editing video. I create comedy skits with my friends for social media as well.
KYLE: Travel, adrenaline-fueled activities, make videos/vlogs, eat ice cream, write, read, have very intellectual conversations, design websites and sales funnels, motivate and inspire people.
What are you best at?
ALYSSA: Motivating people! I am best at creating positive energy in a room and transforming people’s minds to believe in themselves.
KYLE: Sarcasm, blind dates, interviews.
What do you suck at?
ALYSSA: I am vertically challenged, so reaching things that are high up. I need a step stool.
KYLE: Speaking Spanish. Working on it, though. Then, probably sewing and tap dancing.
What are you looking for in a date, physically and/or otherwise?
ALYSSA: A fun conversation, but none of that surface level bulls**t like about where you went to college and what you do with your buddies on the weekend. I like a deep intellectual conversation.
KYLE: Great conversation, good food, top-notch deeper-than-surface-level interview questions, and at least one “test” that allows us to see if we each take risks and trust ourselves. In a person, I look for a woman who captivates me with her intellect and mindset as well as how she treats other people.
Describe your special brand of sex appeal in five words or less.
ALYSSA: Flirty? Fit?
KYLE: Do you love maple bars?
What do you like least about yourself?
ALYSSA: I can be stubborn.
KYLE: I am my biggest cheerleader who sometimes has to kick myself in the ass for getting down on myself and preach to myself when my thoughts try to pull some negative BS on me.
Rate yourself on a scale from one to 10 for looks.
ALYSSA: “Shawty is a 10.” — The Dream.
Rate yourself on a scale from one to 10 for personality.
ALYSSA: I have been told I have a lot of personality!
KYLE: 9.989. I’m not perfect, don’t judge me, but I strive to be outstanding.
What traits might your date exhibit that would be complete deal-breakers?
ALYSSA: I am more confident, independent and self-aware than most men.
KYLE: She starts talking about how she is a Satanist. Yep, I would pray for her, then leave. If she has more butt pictures then face pictures on Insta and is looking for validation through social media outlets.
How many people have you slept with?
ALYSSA: I enjoy relationships and long-term commitments.
KYLE: I was a douche in college. I enjoy the beauty of monogamy now. I was born to make mistakes, not fake perfection.
Fill in the blanks: I want my blind date to be “blank” and “blank.”
ALYSSA: Funny and charming.
KYLE: Hilarious and driven.
Will the night end with a kiss, something more or something less?
ALYSSA: If he is lucky, he will get my phone number. Other than that, he’s just a stranger.
KYLE: If it’s a kiss, cool. If not? Cool. I respect her and her boundaries. I am more interested in getting to know what goes on in that thing between her ears first rather than getting to know what goes on with her between the sheets.
What’s the most important thing in the world?
ALYSSA: Love, gratitude and happiness.
KYLE: My faith. And maybe maple bars.
An EPIC Limo arrives at Alyssa’s Bay Ho home before picking up Kyle from his place downtown. First up on this evening’s agenda is a stand-up paddleboarding session off the coast of Coronado. The owners of SUP Coronado were kind enough to hook up our daters with a couple of their best boards, and after quickly recapping the fundamentals of staying afloat, the daters make their way down toward the water.
WET ‘N’ WILD
Alyssa and Kyle dip more than their toes in the water.
The glassy San Diego Bay is relatively calm as the two begin paddling toward the Coronado Bridge along the city’s immaculate skyline. Kyle’s a bit nervous, as this is his first-time SUPing in a long time, but Alyssa, who’s attempted it before, tries to assuage his concerns. And while Kyle does quickly find his footing, it doesn’t take long for Alyssa to lose her balance and wind up wet. The daters drift past sailboats and under the bridge, and just when Kyle thinks he’s in the clear, he does lose his cool and end up drenched.
After an hourlong excursion on around the Big Bay, the daters head back toward dry land and change out of their salty duds and into some proper evening attire. Next up is dinner at Imperial Beach’s exquisite new seaside eatery, Verandina.
A two-story seaside restaurant serving handcrafted Italian fare in the heart of Imperial Beach, Verandina provides guests with elevated dining experience against a backdrop of beautiful ocean views. Signature dishes include octopus a la plancha, truffle arancini and linguine ai Ricci among other mouthwatering menu options. After Alyssa and Kyle order drinks and apps, we split them up for mid-date debriefings.
How’s it going so far?
ALYSSA: It’s going awesome. Paddleboarding was a lot of fun, we were making fun of each other this whole time.
KYLE: It’s going wonderful. She’s awesome. She’s cool. Good conversation, great personality.
What were you first impressions of your date?
ALYSSA: I thought he was really funny, sweet. He’s sarcastic like me, which is easy. Super cute.
KYLE: We started talking slowly, and little things she’d throw out, I’d think that too. So I kind of understood that she had the same mindset about life and some things, simple things that it’s easy to talk about.
Is this the type of person you’d normally date?
ALYSSA: I look at personality first. That’s super important to me. Is this someone I could hold a conversation with about intellectual things or about life? Definitely. So, I just like who he is, or who he’s shown me, at least.
KYLE: Yes and no. Yes because, mindset-wise, we’re entrepreneurs, building businesses, want to make people’s lives better. No, as in fitness. It becomes a religion to stay very committed to that. My fitness journey is different. I work out once or twice a week, three times a week, just so I can continue to stay healthy.
How was your experience at SUP Coronado?
ALYSSA: (Laughs) I feel like we were way too hooked on talking to each other than actually trying to paddleboard. We were going in circles. It was fun, but I definitely need more practice. The instructor (Vicki) was also super nice.
KYLE: Awesome. Vicki was awesome; she was so funny.
How is your experience at Verandina?
ALYSSA: The service is great. The owners made sure we were OK and our server Madison is awesome. And the food is amazing. I love the crab gnocchi. The prosciutto bruschetta is really good.
KYLE: I haven’t had Italian food in so long. It was so good. And the fact that it’s in Imperial Beach and not the typical Little Italy or somewhere else, it was very good. The Pellegrino was delicious. The lime was fabulous.
What’s the most attractive thing your date has done so far?
ALYSSA: He genuinely looked at me and said I was beautiful. It was really sweet.
KYLE: Most attractive thing? She smiles a lot. I like people who smile because it means they have a bright personality.
What’s the least attractive thing your date has done so far?
ALYSSA: I don’t think I could find anything.
KYLE: She doesn’t have one. She’s pretty cool.
Rate your date on a scale from 1 to 10 for looks.
And for personality?
What’s your date’s most attractive quality?
ALYSSA: I like his smile.
KYLE: She’s in shape; she works out.
What’s your date’s least attractive quality?
ALYSSA: I don’t like to focus on those types of things. That’s just not me.
KYLE: She doesn’t have one.
Do you want to kiss your date right now?
ALYSSA: Maybe the next date or five. I don’t like to kiss on the first date.
Does your date want to kiss you?
ALYSSA: I mean, who wouldn’t?
KYLE: Probably not. Maybe.
How and when will the date end?
ALYSSA: How? I feel like we could either go somewhere and talk and hang out more — somewhere fun. Or I could see us just exchanging numbers, going home and maybe hanging out another time.
KYLE: After this, we have the limo for a couple more hours. We’ll probably see the city.
Daters feast on Italian fare before calling it a night.
How was your experience and dinner at Verandina?
ALYSSA: It was awesome. It was cool because we got to eat upstairs and it was such a beautiful view. It was intimate because no one was up there. The food was awesome. A great experience.
KYLE: It was delicious. I have not had Italian food in quite some time, and that place was the perfect place to have Italian food. I love checking out new places. The food was incredible and dessert was delicious, too.
What did you eat and drink there?
ALYSSA: We got to sample some Italian sodas, and then I had the prosciutto bruschetta, which was really good with a fig jam on it. And then the crab gnocchi, we shared that. And the swordfish and we had lobster and crab mashed potatoes. Everything was super tasty.
KYLE: I had crab gnocchi that was really good, and we shared lobster and crab mashed potatoes.
Where did you go and what did you do for the rest of the evening after dinner?
ALYSSA: I just went home. I was super tired and I had to go feed my dog. But we did exchange numbers and we’re probably going to hang out soon.
KYLE: The rest of the evening was pretty low-key. She has a dog that’s very new, so she had to rush home and let him out. So we just drove her home and called it a night. But we made plans for something else this week, which is cool.
Was there a kiss or romantic exchange?
ALYSSA: A really nice hug.
KYLE: No, there wasn’t.
What’s the funniest thing that happened during the date?
ALYSSA: Probably when I fell in the water right away, but he didn’t fall in the water when we were paddleboarding until much later. I was hoping he would, just so I wasn’t the only one wet. I was secretly waiting for him to fall in.
KYLE: Before we got on the paddleboards, I was telling her the last time I was on a paddleboard, I fell off in, like, two seconds. But she was like, “No, you’ll be fine.” And she got on and fell right off. It took me about 20 minutes before I fell off. So, that was pretty funny, both of us falling off paddleboards.
What was the best part of the date and why?
ALYSSA: Probably when we were just talking about our favorite books and entrepreneurs and sharing our similar interests when we were paddleboarding. Getting to know each other’s family backgrounds and sharing stories of adversity that helped us grow into bigger people. So we definitely established a deeper conversation, which I appreciate.
KYLE: The parts where we were on the paddleboards, paddling. But we were in such good conversation and it was kind of windy, so we weren’t really moving at all. So that was actually pretty cool, because there was great conversation the whole time.
What was the worst part of the date and why?
ALYSSA: When it ended, because I was so tired.
KYLE: Sitting in the back of the car, because I get car sick.
Will there be a second date? Why or why not?
ALYSSA: I’d like to hang out with him and pursue a friendship and then, we’ll see about dates.
KYLE: Yeah, definitely. We’re going to hang out sometime this week. She’s a busy person, I’m a busy person.
What’s one thing your date really should know before going on another date?
ALYSSA: Well, I don’t know. I think he nailed everything. He’s not overly flirty, he’s not touchy. He’s subtle; he’s a gentleman. I’d say, keep it up. Show interest, but not too much. He’s already nailing that.
KYLE: Like advice? Just continue to be herself.
What could have made this date better?
ALYSSA: I guess at dinner, it was a little awkward because we were alone with the matchmaker and photographer. So we were talking super quietly. Not used to that.
KYLE: Helicopter ride to and from.
Anything else you’d like to add?
ALYSSA: Overall, Kyle was a great person and anyone would be lucky to date him.
KYLE: I had a blast, I went in with no expectations and it was awesome. It was a good time.
AFTERMATCH: Well, there you have it. Between a needy dog, a carsick Kyle and a “really nice hug,” a date filled with common ground was brought to a noncommittal conclusion. Hopefully these two do hang out again, and, with any luck, Alyssa will hire a dog-sitter.
Daters’ answers may have been edited for length and clarity.
If you’re interested in meeting a single local looking for love, email email@example.com with a short bio, some photos and a description of your ideal date.
Special thanks and promotional consideration to
EPIC Limo: 858.270.LIMO (5466), epiclimo.com
SUP Coronado: 619.888.7686, supcoronado.com
Verandina: 619.271.6795, verandinarestaurant.com
Matchmaker Jessica Pelligra: matchandmagic.com