#DestinationDating: Water so clear you can see to the bottom. $100,000 cars, every body got em

I swore off destination dating at the end of last year. 

From two trips to Miami (one in which wound up having me get ditched while rocking a bikini), two trips to Vegas (remember the whole puking on hookers thing? Yep. At least I can scratch off having one of "those" Vegas trips), and a trip to Colorado with a dude that was genuinely missing a few screws. 

I can't keep putting myself in these situations, I thought at the end of my last trip. 

I'm done. 

Plus, I'd love to find someone in LA, or at least someone that travels to LA on a semi-regular basis. This is my home, and here is where I want to be for now. 

Flash forward a few weeks later and I actually gave up dating all together. My focus was self, and self only. 

During that time, I had been contacted (through my manager) by a professional matchmaker that was about to embark on a new search for one of her high profile bachelors. This woman is very highly regarded in her field (she even has her own TV show), but doesn't get new media and wanted to maximize her search results for this contest. 

Being a lover of "love" myself, I wanted to of course assist in anyway I could. 

Send me a one sheet, I asked, with pertinent information on the bachelor and how exactly you are executing this search. I'll then figure out how to tell the story of it online. 

Not a problem, she said. 

We then went back and forth for a few weeks/ months. Between her schedule and mine, it wasn't always easy to make things work out. 

Something about this project though kept nagging at me. I don't know why but I needed to be involved. 

I got on this woman like white on rice sending email after email reminding her that we needed to speak. 

We finally got on a call just a few weeks back, and about 10 minutes in she stops me. 

How old are you? 

I'm 28, I said. 

Hmm. I like your age, and I like the way you speak. I think this might work. 

She paused. 

I want someone in my office to send you over an application as well. Who knows, maybe this was how I was supposed to find his true love. 

I laughed thinking the only thing I really know about this guy is that financially he is set. I've dated the millionaire playboys, I thought and they're all fucking pricks. I can't STAND Peter Pan syndrome, and don't want to be a part of it anymore. I'm extremely extremely determined to continue to build my own name professionally and want more than anything just an authentic experience. All history has taught me with men like this is that they are anything BUT authentic. 

The day drew to a close and the more that I thought about it the more that I realized maybe I needed to be more open minded. 

I'm a work-a-holic so maybe this is the way that I'm supposed to meet my dude. He's certainly gotten my attention which is more than I can say for a lot of others. 

I was then sent a series of questions, about my lifestyle, background, family, and future plans. 

I answered them all from my heart, and EXTREMELY specific on what I was looking for. 

My 5 year plan includes a handful of professional goals, but the rest are all personal. I want to get married, and I want kids. It's not going to happen over night, and I TOTALLY get that, but I'm done dating playboys and experiencing just for the sake of the experience. I'm ready to place down some roots. If you're actually serious about that and grounded in general - GREAT! If not, awesome, and good luck on your search. 

<tangent> of course that wasn't the only thing on there. There were about 10 questions total, but I'd prefer not to share that part =) </tangent> 

The next day I got a call saying that I had made it to the next round. 

I was certainly excited but also not prepared for what was next. 

What are you doing with your life, she says causing me to halt to a dead stop in my kitchen. I have to be careful who I let be introduced to my clients, she said, and while we were doing our background check on you I found out that you're a dominatrix? Why are you putting so much of your life out there? What guy is going to be attracted to that? 

Immediately I started crying. 

I don't know why, exactly, but like the inner child work has taught me it was just an expression of what I was feeling in that moment. 

Wow, I said to her. I never cry. I just feel very vulnerable right now. 

I feel like a mother or big sister to you, she said, and the person I've been talking to and see in your photos is not what I've read about you. 

You have to understand though that all of this has been a process. I didn't mean to have all of these super wild sexual stories, it was just part of this curiosity inside of me that I couldn't deny nor do I regret. This is who I am, this is what I've done. Am I a domme anymore? No. I've shifted my focus and if a guy counts me out for that, I can't change it. 

Of course all of that was said through tears and sniffles. It was an extremely, extremely authentic conversation. 

I then admitted more of my truth … 

I don't want this anymore though. I've been doing self work all year and haven't been documenting it all since it seemed to defeat the purpose. I discovered at the end of last year that all I did was build a business around a coping mechanism. This is what i did as a kid when I couldn't understand something, or needed to vent. I had no friends so I just went online and wrote in my journal. The only difference now is that I click publish. 

He's very understanding and open minded, she explained, but I can't make any promises. 

I don't care about that as much to be honest with you, I'm just very thankful for this conversation. I know I need to change certain aspects of my life, even still. 

<tangent> The day this conversation happened btw was the day that I had finished writing out my post about my most recent playboy mansion adventure. Not exactly easy to say "something isn't you anymore" when you are standing there half naked on your own website. Shit. </tangent> 

I spent the rest of the day in a haze. I continued my inner child work, but could barely function outside of that. 

Being someone that always operates in tangibles, the entire thing left me so so so confused as to what my next doable action was. 

How can I prove to men that I can be "taken seriously?" That I'm not a "party girl." My friends will ALWAYS be the first to tell you that. I don't seek all of these wild stories, I just happen to meet a lot of people every day and have very open energy. 

My resistance to accept my part only furthered my desire to want to continue the inner child work. 

The next day I got an email from her office asking me to send over 5 questions for the bachelor to answer. 

This isn't just a one way street, the email explained. 

I then wrote out 5 questions that I would want to know about my mate and the next day while en route to a lunch meeting I got my answer back. 

I sat in my beetle reading the first words from this human being that I had been so focused on for the last few days. 

His voice was pure, and his heart was right there with each scroll. 

It shocked me how much his email affected me. All I do is read emails and read digital interactions, but to have one strike me in such a way surprised me. 

We then exchanged a few messages back (all facilitated through the matchmaker) and agreed to meet over the next few days. 

I'd normally just hop on a plane, I explained, but I have project meetings this week and a charity event on Friday that I've put a lot of heart into. I can't go back on my word and my commitment to both. (Especially since the charity event was in honor of my grandfather.) 

I looked at my schedule and realized I could be there as early as Saturday morning. 

I can be on a 6am flight on Saturday, I indicated. 

Her office then arranged my flight as I had confirmation I would be staying at the St. Regis in Bal Harbour. 

Well this is getting real, I thought. 

The rest of my week went on and I tried my hardest to put this "search" and my own potential matching out of my mind. The matchmaker kept saying over and over that she had a strong feeling on the two of us (as did he as well), but after so many heartbreaks and so so many times I've had my hopes up about something - I preferred to just keep it real and be grateful even for just the expression of authenticity. 

I'm speaking my personal truth to something other than a computer. This is a first, I thought. 

Friday came around before I knew it, and I finally got to put on the dress I bought the month prior for this event … 

It wasn't sponsored, I actually paid for it. Nothing about this event was for business. I didn't bring a single business card, nor did I plan on doing an ounce of networking. I was there to represent this charity, and a cause that I believe in. Whatever is required I will do, but I am not here for myself. This is all just a big thank you to someone that inspired me. 

I invited my buddy Chelsea as my date as she too had lost someone close to her to rectal cancer. 

About an hour before I had to leave for the event, I got a call from my mechanic. 

Your convertible isn't going to be ready today. I just got it back from the window shop and we still need to put everything back together. 

<tangent> This guy is TOTALLY badass btw. Not only did he just give me his car as a loaner, but the first day I went to his shop we kicked it and he even opened up his bar handing me a shot of tequila. (I didn't finish it since I was going to have to drive obvi) </tangent> 

I was frustrated at the inconvenience but laughed at the reality. I'm in this super super fancy dress, on my way to a super super fancy hotel and I'm going to have to take …. this

The car he loaned me had been modified and was a low rider. It's an acura and the steering wheel literally sits on my lap and if I adjust even the seat a little I can't see out of the mirrors. You kinda just have to roll with it, but being SO UNBELIEVABLY white in such an UNBELIEVABLY ghetto-fantastic vehicle made me laugh. 

I might not know how I always end up in these situations, but go me for figuring out how to make the most of them!! 

I put on my Jay-Z playlist on Spotify and creeped down Santa Monica blvd. 

I pimped my hoes, and h-o-v-ed with the rest of 'em. 

I made some new friends in traffic as a few people also laughed at the obvious awkwardness of the situation. 

As I pulled into the SLS hotel, the valet laughed as I walked out. 

You are not what I expected, he said still laughing. 

I thanked him as I walked inside meeting up with the rest of the host committee. 

This night really meant a lot to me. My grandfather always taught me to be logical and go after anything in life that was just going to make me money. On his deathbed, however, and after he had spent so much time chasing things instead of enjoying them - he changed his tune. 

Follow your dreams, he advised. 

Seems so simple, but coming from him it had a tremendous tremendous impact. 

The night went off without a hitch. It was AMAZING to see so much hard work pay off (and even be able to hook everyone up with a ride home courtesy of one of my favorite sponsors LYFT!!). 

Again, I never once walked the red carpet, never once handed out a business card. Very hard for a shameless entrepreneur but felt great as the granddaughter sending a loving gesture to her grandfather. 

About halfway through the event, I left Chelsea and went to go and get a drink. 

As I turned around from where we were sitting and walked about 20 steps I spotted a familiar face. 

I literally did a captain obvious double take. 

HOLY CRAP, I thought, that's STEVE WARD!!! 

See, Steve is not only the extraordinarily charismatic host of Tough Love, but I asked him out on Ustream a few years back and even got the entire trip sponsored. He was super chill about the whole thing, and even let me be a guest on his radio show. 

I went to the restroom collecting myself, and walked back over calm and confident. 

I am on the HOST COMMITTEE!!! This is MY turf now!!! 

</tangent> Also kinda hilarious to tell this extremely dramatic story of going across the country just to meet someone (sleeping in airports, crashing on couches, borrowing cars from amazing amazing members of this community) and then wind up in the same room as them a short time later. </tangent> 

I outstretch my hand as I say … 

Steve Ward. Jen Friel, how are you? 

Thinking I am going to have to explain where we met, I almost continue … he cuts me off. 

Jen Friel. You just met with a very good friend of mine, he says walking through the crowd towards the bar guiding me and his friend whom he has yet to introduce me to. 

Your hair looks darker he says, still walking through the crowd. 

Nope, I said. You said that last time too. Same hair color. 

No, he reaffirmed. It looks darker. 

Nope, I said, again. Same color. Just like before. 

You sure it's not darker? 

I stared.  

Steve is as devastatingly gorgeous in person as he is on TV. 

He breathes this air of confidence that I've always found alluring. 

We chatted for a bit. I was finally introduced to his friend who was quite sweet and equally attractive. 

Throughout the night, Steve kept coming up and we would chat. This kind of attention I would have KILLED for in the past, but in my current state - I was kinda over it. I don't want the "house of cards" facade anymore. I'm seeking authenticity on all fronts. 

What Steve represented to me was a projection. While humping holograms may be a fun pastime, it's not where I want my future to go. I want real. 

A few hours later, I peaced out to finish packing and head to the airport. Because my flight was at 6 am, my wake up call was set for 4am. Anyone that knows me, knows that I am NOT a morning person. At all. 

To sustain functionality, I decided to crash on the couch to not fall into "too deep" of a sleep for those few precious hours. 

By 5 I arrived at the airport and hungered for some trail mix before the flight. 

<tangent> Trail mix is AMAZING to travel with btw. It fills your stomach without making you "too full" causing any sort of coma. </tangent> 

I went over to the Hudson News and searched for a bag of "energizer" trail mix with the sweet sweet chocolateness. 

As I grabbed the bag and headed over to the register I spotted a familiar face. 

It was the last two covers of Sports Illusatrated Swimsuit Edition staring back at me IRL. 

Ms. Kate Upton. 

She was in a simple black turtleneck, jeans, boots, with her hair back and no make up with her friend. They purchased three copies of Lean In by Sheryl Sandberg. 

Look at that, I thought. Models do read!!! 

Kate is as beautiful as one would expect, but there is something very - ordinary about her. Living in LA and NYC I've seen countless models before in the wild, and there was very honestly nothing spectacular about her beauty. I find her boobs to be ABSOLUTELY FABULOUS and her overall marketing for her brand to be brilliant - but the rest? I have to admit I wasn't that impressed. 

I partially assumed she was going to be on my flight (since Miami is also a celeb hot spot) but the rest of me didn't care. I had three objectives:

1) Food in my belly.

2) Get on plane.

3) Fall asleep.

I got to Miami a few hours later, and was instructed to meet my limo driver down by baggage claim.

<tangent> Yes, men also send town cars. It's actually quite awesome to avoid the whole awkwardness of just meeting someone and then having to sit in a car with them for however long. Very smart to just send a car if you can afford it WHICH these men that fly you out for a date and put you in a 5 star hotel definitely can. </tangent>  

I was super super nervous at this point going into this date TOTALLY blind, but also relieved to know that I was making a big move being so vulnerable in both an emotional and physical sense. 

I sat in the lobby of the hotel waiting for my room, and my date. 

I was excited because IT WAS SO SHINY!!!!! 

The St. Regis in Southbeach is GOORRGEEEOOOUUSSSS!!!! 

A few minutes later, my date arrived. 

Even though I had no idea what he looked like (as I was not sent a picture), when he walked in - I pointed and called out his name (he had texted the day before and revealed his first name). 

And the rest? 

This is all you get ... for now. 

I can genuinely say it was HANDS DOWN one of the best weekends of my life, and definitely the most authentic. I'm EXTREMELY stubborn and hard headed, to be proven wrong that a guy like this could BE so down to earth and humble truly moved me. 

We share almost identical emotional life experiences just cut from a different cloth. I reconnected with an old friend that I just hadn't met yet in this life. 

We talked, and talked, and talked. There was only one fancy dinner, and it was at the JG Grill, not Nobu or whatever the latest and greatest place to "see and be seen" on Southbeach is. 

Everything about this experience was real. Very very real. 

I can say one thing that was HILARIOUSLY funny and in true "Jen For-real" form ... 

I commented on a Ferrari as it was pulling out of the St. Regis.

UGH! I said, sitting in his jeep. I don't understand how anyone can spend 200K on a car that the second you pull it out of the lot depreciates so much in value. Such a waste. 

He turned, smiling and saying that this car was worth even more. 

Smooth Friel. Smooth. 

His car was chill though ... it was a jeep that was INSANELY pimped out. This guy doesn't need to floss, he's actually extremely embarrassed by it. That turned me on SO much more as it speaks to his confidence and true character. 

This is real, I thought. This is very real. 

My flight is booked to head back and see him again next week. 

As for the rest? 

We shall see. I know I'm not scared to be vulnerable anymore. That pleases me. 

And so it is. 

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