Illustration by Ross May

There we were, my date and I, standing in front of a bungalow wine bar, staring at our phones, commenting on expected Uber arrival times and bemoaning their wrong turns. Our conversation over two glasses of pinot noir had been lively, our connection promising. But now we were sucked into our screens, and I realized I had no idea how to break free and lean in for that first kiss.

I live in Los Angeles, so most of my dates have ended with us walking back toward our cars. At some point comes the moment of truth. If she turns toward her vehicle, I get the message. If she lingers and makes eye contact, I have an opening if I want to make a move.

Or at least I used to. Ride-hailing apps have not only changed cities; they’ve also changed the dynamics of dating, especially because going out with someone generally involves leaving the house. Not having to worry about driving is a huge benefit. But Uber and Lyft also transform a crucial moment of courtship into an awkward technologically influenced anticlimax.

Daters do have more autonomy: You can drink without worrying about driving drunk, paying hefty cab fares or waiting late at night for public transportation. If you find yourself in a sketchy situation, now you have an escape button.

“I love having that sense of safety, especially if you're meeting people online,” says Bruna Nessif, founder of the website The Problem With Dating. “You don't really know who that person is on the other side of the screen.”

With this convenience comes new complications, and not all involve kissing. I spoke to dating experts and Uber drivers to answer all of your potential questions on how to handle them.

When should you go for the first kiss?

Dating experts offer conflicting opinions. (I knew my awkwardness wasn’t unfounded.)

“I think the best time to make a move would be right as the Uber is pulling up,” Nessif says. “You don’t want to do it too early because then if it goes left you’re just stuck standing there. It’s like, ‘No, thanks,” and then you’re like, ‘Cool, cool. Oh, your Uber made a wrong turn? We’re going to be here a little longer.’”

Or you can try before you’ve even called the car. “If you want to kiss,” says dating expert Adam LoDolce, “don’t wait until you’re on your way towards the exit because it creates so much pressure on that situation.” Better to make your move while sitting next to each other at the bar.

Regardless, don’t just stand there staring at your phone. Look at how long the car is going to take, stick your phone in your pocket and focus on your date — and if you don’t see the driver, they’ll call you.

How about sharing an Uber?

If you’re both heading the same direction, do a solid for the environment and put two destinations into the app.

“Thinking of chivalry and all of that, I would say you should drop the girl off first,” says Nessif, assuming she’s not too far out of your way. “The ideal situation is, the guy gets out and opens her door. So there is the opportunity if you wanted to kiss her or say whatever you wanted to say. That would be a little more intimate than doing the side hug in the back and being like, ‘Cool, thanks.’ ” (Of course, if you’d prefer not to follow traditional gender roles or are not a heterosexual couple, either partner can do either part in this scenario.)

Dating and relationship expert Hunt Ethridge agrees: “Make it for two stops,” he says. This also gives your partner the opportunity to invite you in without feeling pressured. “If you get lucky, you lose five dollars. And I think that everybody is okay with that.”

What about making out in an Uber? Is that cool?

No.

You sure about that? People mess around in cabs all the time.

Uber drivers have surprisingly few stories of passengers making out. There are exceptions — twice I heard something along the lines of “One time my friend who also drives for Uber had two people really getting it on” — but it’s generally just not something that is done.

“If you’re a cabbie, you’re going to be dealing with people getting frisky in the back seat,” Ethridge says. But cabs often have that wall between the front and back. Ubers, not so much. “Your elbow could accidentally brush somebody’s knee as you’re driving.”

Should you offer to pay for your date’s Uber?

“It’s a chivalrous thing to do,” Ethridge says. “It’s another version of buying flowers or opening doors and pulling out chairs.”

But paying for your date’s ride should never be expected, Ethridge says. It’s more like picking up dessert after the other person buys dinner. Offering to pay for your date’s Uber is not a gendered move so much as one other way to show appreciation.

Still, you are asking the other person for an address, so proceed with tact — don’t push it if they decline.

What’s the deal with people on dating apps touting their Uber ratings?

Uber ratings often appear on profiles, usually as the kicker, the last line that tells the world you don’t take yourself too seriously. The problem is, it’s not an original move. You’re right there with the people who say they’re looking for someone to “save me” from the app or the men who give their height “in heels.”

“If the thing that you have most to brag about is your Uber rating, then you need to go get a life,” LoDolce says. “Hopefully you have more accomplishments in your life than your 4.83 Uber rating.”

How else has Uber changed dating?

“The radius of dating has opened up a bit,” says Ethridge, who lives in New Jersey. “There is the old joke that, you know, people wouldn’t date below 14th Street” in Manhattan.

Even though Hoboken is right across the river, Ethridge had trouble dating anyone in the city when he was single.

“Previously, it was like 50 bucks in a cab just from like one side of the Lincoln Tunnel to the other side of the Lincoln Tunnel,” he says. “Whereas 50 bucks would take you all the way out to Long Island in that direction [from Manhattan]. So it was very frustrating for those of us here, and basically everyone just signed off on anyone in Jersey like, ‘Yeah, that’s just not going to happen.’ ”

Meanwhile, in Los Angeles, Nessif says a date once impressed her by taking an Uber from Mar Vista to West Hollywood.

“It was probably because I liked him so much,” she says, “but I was like, ‘Oh, my gosh. He took an Uber from the Westside to come see me. How sweet.’ ”

What about hitting on other riders? Or the driver?

Jakisha Chatman has been driving Uber for almost four years. She’s seen plenty of connections made among talkative riders in Uber Pool. If your fellow passengers are down to chat, go for it.

But that doesn’t mean the people behind the wheel are just waiting around for your advances.

A driver named Andrew says he once picked up a gorgeous woman who sat in the front seat on a solo ride and told him all her roommates were models. When she asked him to come upstairs at the end of the trip, he declined. He thought there must be some kind of catch. “It’s never that easy,” he says.

As for Chatman, she wants her suitors to know their online compliments are appreciated but anonymous.

“When you leave a five-star rating, you can leave a comment, so I get a lot of passengers who say, ‘Oh, you’re so beautiful,’ and ask me questions, ‘Are you taken?,’ basically trying to talk to me through the app, and they don’t realize that I don’t know who it’s from and I cannot reply. It just shows me the comment.”

Nice try?