This is an approximation of my experience thus far with Crowdpilot, a crowdsourced conversation app. You sign up, download the app to your iPhone, and tell it what kind of conversation you want to have: a date (iPhone Cyrano, the kind of thing people have experimented with before), a meeting, a "chance encounter," and so forth. After that, strangers plug themselves in to the desktop end of the site, listen to your conversation, and type advice on how to advance your chat. (There's also a feature where you can pay someone 99 cents to guide you. More on that shortly.) Talking with your estranged child? Maybe someone will helpfully type in: "Play catch and promise to be there for him from now on!" Or not. You can see a video of it in action below.

The experience is, uh, pretty awkward. For one, there aren't too many people answering questions right now, meaning you're stuck waiting for a couple minutes, steering the conversation yourself, until someone drops by. In the meantime, you check your phone, which sits between the two of you and picks up the audio. Maybe if more people go in for the app, this won't be such an issue. 

Before you start your session, the app opens a window to make sure everyone involved in the conversation knows they're being recorded. I can barely imagine a situation where someone didn't realize the person opposite them was reading questions off their phone, but it doesn't matter: this is more of a game than a way to seriously get consultation for your issues. (Although, with advice categories like "argument" and "consolation," I'm not sure the creators of the app see it that way.)

I wiretap-chatted with PopScions about their Valentine's Day plans, while being fed cues from someone in another part of the world. What follows are edited and shortened snippets of the conversations we had. For the first two, I enlisted the help of a stranger (who I believe but can't confirm was the same person), and for the third I ponied up 99 cents for the advice.

Intern Gabe Bergado:

CUE: sunny day today huh?

Gabe: Not really.

Colin: Yeah it's actually kind of the exact opposite of that. It's actually been incredibly snowy outside, so I don't have any idea why I said that.

[silence]

[conversation continues]

CUE: Do you have any big Valentine's Day plans?

Gabe: Well my roommates and I have a reservation at White Castle tonight.

Colin: That is a bizarre Valentine's thing, but that's good! Have you been before? It's a wonderful place.

Gabe: None of us have ever gone, but we saw White Castle is doing special reservations with white-cloth linen.

Colin: That's an amazing thing.

Gabe: Some McDonald's are also doing reservations!

Colin: I've only been to White Castle two times, but both times it was a terrible experience. So that sounds like an awful plan. Your Valentine's Day is ruined.

CUE: Was it hard to get a reservation there?

Gabe: Yes, actually. All the ones in Manhattan were already booked, and this was two weeks ago, so we had to go to one in Brooklyn.

Editorial assistant Lindsey Kratochwill: 

Colin: So what's new?

Lindsey: One of my neighbors is coming to town this weekend! It's actually kind of strange because they're coming for Valentine's Day and they want to take me out to dinner tomorrow, so I'm crashing their Valentine's Day trip.

Colin: At least it's not a super-romantic thing where you're sitting in the middle of them at a table or something.

Lindsey: Well it could be, I don't know.

[waiting for cue]

CUE: say something personal

Colin: Um. Uhhhh. I personally will probably binge-watch television this weekend. Because that is something I do an almost unhealthy, inordinate amount. I feel like lots of people do that, and they probably have these exact same feelings, but sometimes I wonder if I'm on the lower end of the bell curve for that.

Lindsey: I would say binge-watching television or streaming video is common. 

Colin: [angrily] Sometimes I just feel like I'm too attached to my devices.

Paid 99 cents, with editor Corinne Iozzio (many more cues were given with this one):

CUE: How about green flowers?

Colin: What are green flowers?

Corinne: I don't know. All flowers have green in them. 

Colin: But there are no blooming flowers that are green.

CUE: a venus fly trap?

Colin: a venus fly trap!

CUE: DO YOU BOTH HAVE VALENTINES DATES?

Colin: Yeah. I do, what about you?

Corinne: We're getting haircuts.

Colin: Matching haircuts?

Corinne: We both very much are in need of a haircut, and it turns out very few people try to get their haircut today. But at least we'll be together! 

[conversation moves to new House of Cards season.]

CUE: Haircuts? Can that be romantic? 

Corinne: Um... no?

Colin: I'm trying to think of things less romantic than haircuts and I can't do it.

You can help and/or receive advice here. Enjoy the new House of Cards or being with your favorite person.