Direct From New York to San Fran for Love: A Matchmaking Experiment

PHOTO: Sixteen New York women signed up for the chance to take on a bi-coastal matchmaking experiment.PlayLaura Reddy/ABC
WATCH Flying Across the Country for a First Date

Connecting New York women to men in the tech mecca of Silicon Valley so both can meet suitable singles to date sounds like a plot from a cheesy summer rom-com, but in fact, 16 women signed up for the chance to take on this real-life bi-coastal matchmaking experiment.

The founders of the dating start-up The Dating Ring recently launched a campaign to fly single New York women across the country to meet San Francisco men in a whirlwind weekend of dating.

Co-founders Lauren Kay, Katie Bambino and Emma Tessler launched the start-up first in New York City. The service typically matches people in the same cities, but as their business grew, they noticed that more women than men where using the service in New York, and in San Francisco, they saw the opposite.

"In New York, we had twice as many women signing up as men. In San Francisco, we had almost twice as many men signing up as women," Kay said, so the duo put two and two together and expanded the company to San Fran.

Looking to bridge the gap between the two dating pools, Kay used the crowdfunding site Crowdtilt to launch the "Cross-Country Love: Help Fly NYC Women to SF" campaign. Through Crowdtilt, they raised more than $10,000 to fly 16 single ladies from New York to San Francisco for a long weekend of first dates.

The women were given four days to go on two one-on-one blind dates with different men, mingle at a massive party, and then take a day to reconnect with a man of their choice.

"Nightline” was along for the ride as these East Coast ladies traveled almost 3,000 miles to take a chance on love in Golden State, and at least one of the women decided to take the long-distance plunge. Watch what happens on “Nightline” HERE.

Traveling across the country to meet someone for a blind date can be daunting, to say the least, and if that first date turns into a long-distance relationship, it takes commitment, but Tessler offers her tips to help couples navigate those unsteady dating waters. Click through the next two pages to find out more.

5 Things You Should NEVER Do on a First Date

1. Never Trash Talk an Ex

"Here is what happens when you trash talk an ex," Tessler said. "1. You sound like an a------. Trash talking of any kind makes you sound like an a------. 2. Your date will immediately think, 'Is that how they’re going to talk about me someday?' 3. Did I mention that you'll sound like an a------? ... It doesn't matter if they were the worst ex in the entire world -- be graceful."

"If you simply have to bring up an ex, whether to explain that prominent tattoo of their name, or because you really want to tell that story of how you saved them from pirates in the mountains of Bhutan, be nice," she added.

2. Never Order For Someone (Without Asking What They Want First)

"People have mixed feelings about being ordered for," Tessler said. "Some folks think it's hot to see their date take charge, others think it's antiquated and rude. But everyone agrees, if you're going to order for someone, make sure you know what they want. It's always awkward when your date orders you a shot of expensive tequila before you get a chance to tell them that you will definitely, 100 percent, throw up all over their face if you take it."

"Did this specific experience happen to me? Maybe. Was it at least their shoes instead of their face? Yes," she added.

3. Take Your Phone Off the Table and Put It in a Pocket/Purse/Garbage Can

"Looking at your phone during a date makes you look disinterested and shallow," Tessler said. "Are you disinterested and shallow? Maybe. But excuse yourself to the bathroom to check Instagram or text an SOS to your roommate. Do not do it at the table. This is mean."

"Oh you aren't looking at it? It's just sitting on the table lighting up and buzzing and notifying you of the other things going on in the world besides the real live human sitting in front of you? This is still mean," she continued. "The real live human will probably 1. be offended, 2. be too distracted by your pocket robot to notice all the other wonderful things about you, like your beating heart and the blood running through your veins. And this will cause them to ... politely excuse themselves and run to the bathroom to text their roommate 'OMG. SOS. They just keep looking at their phone blowing up on the table. So rude. I've got to get out of here.'"

4. Never Be Late

"This isn't just for first dates," Tessler said. "A person's time is valuable and they used some of that ultra-valuable time to make sure they were on time for you. They checked the train schedule and allotted extra time for delays and made sure that they were at the bar 10 minutes early, sitting in a flattering position, nonchalantly reading a book that they would never ordinarily read, so that when you roll up, there is a punctual, good looking, intellectual waiting for you. The least you could do is show up on time."

"Besides, you only get to make a first impression once," she added. "And being late guarantees that you will come off either 1. rude, or 2. really sweaty and out of breath. Gross."

5. Don't Decide on the Person Within the First Two Minutes of Meeting Them

"Remember that time in college when you were at that party and that guy was flailing around on the dance floor to that one MGMT song? And you thought, 'Hey Super-Sweaty-American-Apparel-Model-Reject, could you flail a little less?' And then you dated him for 2.5 years? You are not alone. We've all been there. So let’s give our post-college dates the same leniency," Tessler said.

"That person you met online might not wow you when they walk in the door, but that's OK. Crushes can take a while to blossom," she added. "Think of it this way: there are a whole lot of weirdos out there. If your first date is with someone who you could see yourself hanging out with, even for another hour, then give them a second date. It could be really really really worth it. And if it's not, then it’s just an hour of your life. Besides, if you showed up late to a date and put your phone on the table and started trash talking your ex before you ordered a round of tequila shots, wouldn't you want someone to give you another chance?"

5 Things Couples Should NEVER Do in a Long-Distance Relationship

1. Cheat

"This sounds pretty obvious, but I'm still going to mention it. This is an extremely bad idea," Tessler said. "Even if you mess up once and you're wasted and no one ever finds out, you will still know. You'll know how easy it is, and then every time you talk to your significant other, you'll wonder, 'Did they hook up with someone last night?' If you're capable of it, what's to say they aren't? And so begins the spiral of doubt and generally yucky feelings."

2. Drunk Dial Your Significant Other and Tell Them What a Hard Time You're Having Not Cheating, and Then Expect Them to Congratulate You for Your Iron Will

"Don't do this," Tessler said. "Yes, it's hard to be drunk at a bar when you’re really far away from your S.O., and yes, you're doing the right thing by not making out with the extremely gross man buying you Fireball shots. But you do not deserve a medal for this. This is basic human decency that you are displaying, and people don't get commended for basic human decency."

"Furthermore, if you would like some praise, ask your roommate/friend/the bartender who is plying you with cinnamon deliciousness. Do not ask your significant other," she added. "The moral of this story is that you should never drink and dial."

3. Don’t Be Jealous of Their Happiness

"Social media makes this one really hard," Tessler said. "It sucks to be across the country from the person you're dating and have to see all their Facebook pictures of happy-laughing-without-you-fun. But try really, really, really hard to just be happy for them. It's good that they're happy. It means you're not in a codependent relationship where you both stop getting out of bed and subsist only on microwaved rice when you're apart. Congratulations!"

"If you get jealous every time you see them having a good time, it is basically 100 percent guaranteed to breed resentment," she continued. "Your significant other has to be able to tell you about the great alligator barbeque they just came back from without worrying that you'll freak out about the hunky alligator hunter. Basic stuff, you guys."

4. Don't Forget To Have Your Own Life

"It's not fair to put your entire existence on one person," Tessler said. "And sometimes in long-distance relationships, that happens. You become so consumed with missing the person that all you do is pick out new emojis to send them. You have become a really dull individual. Your friends will starting calling you Ol' Boring Dull Face behind your back... So go! Have a life! Have fun! Your relationship will do better because of it."

5. Don’t Spend All Day Texting

"Even if you have a life, you might find yourself texting your lady or fella all the live long day, because it's nice to stay in touch. I get it," Tessler said. "But then when you sit down to have a good long Skype session that inevitably turns into some steamy Skype sex, you realize you have nothing left to say to each other, because you've been talking all day, then you'll feel like you lost the spark, and you didn't. You just channeled it into your phone, instead of into the other person."