KATIE: AHAHAHAHAHA. HAHAHAHA. Oh my god. Oh my god. Mike is too creepy even to deal with. He has terrible hair and terrible clothes. In this picture he is four years shy of becoming a self-styled pickup artist.
ADAM: Oh no, no no nooo. Mike is smiling like he was never supposed to be part of this game, but he snuck in anyway. I can’t tell if he has really thin, wispy bangs or what. Mike is a disaster.
JEN: I’ve had one wart in my life. It was on my foot. I went to a pediatrist and he wouldn’t stop petting my toes. I’m pretty sure that pediatrist was Dream Phone Mike.
KATIE: Carlos issssssss up to no good. I do not trust that one dimple. At all. I bet he has a mullet and his popped collar is obstructing it. He is bad news. If my friend had a crush on Carlos I’d be like, “Girl, no.”
ADAM: Oh, poor Carlos. He doesn’t like like he reads much. His mom probably cuts his hair. I feel bad for Carlos. He never stood a chance in this world.
JEN: Carlos just wants to take you to the slopes, y’all. Let Carlos take you to the slopes.
KATIE: Lmao. Phil. Your little straw hair and braces and Harry Potter glasses. Let me copy your science homework.
ADAM: Phil probably has a lot of books on how to seduce women. I bet he tucks his pants into his socks. At the same time, I feel like he might surprise us all and grow up to be a stud.
JEN: Heh. Phil. There’s not much more to say.
KATIE: No. There is no question in my mind that Dave laughs like “Heh heh heh.” And makes jokes about like, what it takes to screw in a light bulb. Dave is devoid of sexiness.
ADAM: I feel like Dave could grow on me. Dave is always the wing man to a hotter guy and doesn’t get much play, but that’s what I like about him. He’s a dark horse. I bet if you took him home, he’d impress you.
JEN: Dave has the worst phone number. He’s probably the subject of a lot of prank phone calls. I feel bad for Dave.
KATIE: Well, this is a 9 year-old. It’s inappropriate even to comment. But I bet his teacher thinks he’s a very smart and promising young man.
ADAM: I will not comment on Bruce because he’s a child. Come back in 9 years, Mike. Then we’ll talk.
JEN: No, Bruce, I will not buy you alcohol. What? You want me to give you my bra? Go home, Bruce. Your mother is worried.
KATIE: Bob is legitimately minutes away from committing a misdemeanor crime of some kind. Possibly exhibitionism.
ADAM: Bob is trouble. Bob sends nudes without you asking. I’m sort of into Bob and I’m 100% ashamed of myself.
JEN: Bob is 19 years older than everyone else. I will never be old enough to date Bob, just as I will never be young enough to date Bruce.
KATIE: He has a penetrating stare that I am not comfortable with. I sort of see him being the kid in the cafeteria who is always trying to trade his lunches with people? And you’re like, “Alan, that’s not a thing, I don’t want to trade you my lunch.”
ADAM: Oh, whaaaaat. Alan, no. Where did you come from? Get out of here, Alan. You’re embarrassing all of us.
JEN: Alan went missing from my Dream Phone box long before it came into my possession, and I’m pretty sure it was on purpose. He’s probably glaring at a Doodle Bear in the back of my sister-in-law’s childhood attic. Good riddance, Alan.
KATIE: George needs to put down the Sun-In and try a different hair place. Good eyebrows though.
ADAM: George looks sweet, but almost too sweet—like he’d get attached way too quickly and you’d have a hard time trying to let him down. George probably always wants to be little spoon. But yeah, good eyebrows. I’d like to brush them with a Barbie comb.
JEN: George is that guy who asked every single girl to the 8th grade dance. They all said no because they knew what he was doing. George is now the CEO of Tinder.
KATIE: I am not SUPER into the button-down over turtleneck look going on here. At all. But I like that he looks a bit mischievous. He’s smizing.
ADAM: Absolutely not. I’m sorry. Are those suspenders?
JEN: I think John might be cute underneath that Urkel-inspired outfit, but I’m blinded by that sliver of a yellow turtleneck.
KATIE: Paul is like, “I’ve got this great new record, you have to hear it. It’s Dave Matthews Band.” I hate him. He thinks he’s really sensitive but actually he is just self-pitying.
ADAM: Paul looks like an egg with a wig. If any of these guys have a pet iguana, it’s Paul.
JEN: I have a soft spot for this one. I used to date a guy named Paul. He kept a photo of me in his wallet, so I kept Dream Phone Paul in my wallet. That’s why he’s so worn out — he went everywhere with me for two years. That being said, Dream Phone Paul has a suspicious lean, like he just farted, blamed a puppy, and tried to change the subject to how well he would have fared on last night’s Jeopardy.
KATIE: Wayne looks like he knows how to party. That jacket? That half-laughing smile? He would be fun. I would go to a kegger with him for sure.
ADAM: I’m having a hard time forming an opinion on Wayne either way, which probably says a lot about him. His face is pleasant but sort of forgettable. He probably has a lot of cool CD’s though.
JEN: Wayne will convince you that you didn’t make a complete drunken fool out of yourself last night, even though you definitely did. Waynes are important.
KATIE: Gary is such a nerd. He is so earnest. Look at his little purple turtleneck. I actually would like to see his teeth because I feel that could really swing my opinion strongly one way or the other. Gary, show me your teeth!
ADAM: Gary only wants to talk about computers. He’s really into the internet, but this is 1996 and nobody really cares about the internet yet. He’s probably a billionaire now and he won’t return your drunk Facebook messages.
JEN: Is Gary wearing a blazer over a turtleneck? Gary has places to go. People to see. Smug smiles to smile. Gary now owns 14 private islands and a fleet of custom built Inspector Gadget yachts.
KATIE: James is probably one of the best-dressed in this crowd, honestly. He’s pretty dorky, but I like that he’s laughing in his picture. I’m not attracted to him but I would want him in my prom party.
ADAM: I would *not* want him at my prom party. He’d be annoyed that there’s alcohol in the punch and probably rat me out. He’s well dressed (at least in terms of the other guys we’re working with) but it’s all a little bland. If I reached into his jacket pocket I bet I’d find a deck of Magic: The Gathering playing cards.
JEN: I went to an all-girls school. Prom was boring. I’ll take as many fictional ’90s board game boys as I can get. Especially James.
KATIE: Haha, I mean. There have been like 18 Tonys with earrings I’ve had enormous crushes on, so. Throw him on the pile for all I care.
ADAM: Tony looks like that “bad” kid who’s just misunderstood. Your parent forbid you to see him. Maybe he pierced his own ear with a safety pin. In a couple years he’s going to be a huge pothead. Maybe he’ll have really really short dreads.
JEN: Tony was born for those old Disney Channel original movies where the kid gets kicked out of math class, dramatically hops over a railing, and launches into a really moody rollerblading montage.
KATIE: Spencer is the ROTC kid in the group, I think, but then it’s confusing because he appears to be wearing a floral print button down under some kind of shiny sport jacket? That’s a very hip, of-the-moment outfit. He has edgy taste. He’s a little awkward but I bet he ages well.
ADAM: I feel like I’d keep hooking up with Spencer and wonder why every time. He’s got an allure. He’s not great but he’s something to do while you wait for Dan. That jacket is on point. The hair is terrible but I like his head shape.
JEN: Spencer is cute, but his face is full of pointy edges. He’s kissable, but you’d risk being impaled by his hair, nose, left cheek, right cheek, or chin.
KATIE: Mark is okay. He has a cool shirt. He is the kind of boy that probably got really, really hot 10 years after this photo was taken. Unfortunately, this photo is all we have to work with.
ADAM: I’m having a real hard time with that shirt. That whole “funky color blocking” thing is a total red flag. I imagine it’s tucked into black slacks and he’s wearing a really thin, shiny belt and probably square toed shoes. Mark is a nerd. Sorry Mark.
JEN: I’m having a fine time with that shirt and a great time with those dimples. Mark is definitely a babe now. Definitely.
KATIE: Steve is supposed to be the skater boi of the Dream Phone world, his hair cut, in ’90s terms, is very on-point. If he had been in a Disney Channel original movie I would have been like, “Ooooh, he’s cuuuuute,” and then forgotten about him.
ADAM: Steve looks like one of his parents might’ve been a velociraptor. He looks slippery. His face has a lot of twists and turns and dangerous angles and he makes me nervous.
JEN: Steve is that guy who got you secondhand high for the first time while you were waiting for your mom to pick you up from clarinet practice.
KATIE: I always felt that Scott was SUPPOSED to be the dreamboat, because he looks like a Ken doll that’s been animated in a lab. So I always rated him pretty lowly. But you know what? He’s a good-looking kid. That’s a crisp collar and a good blow-dry.
ADAM: Scott is the second best of all the dudes. He looks like he’d take care of me. He owns a pair of really expensive boat shoes and maybe even a boat. He speaks French, maybe. Take me, Scott.
JEN: Scott already has a girlfriend. You can tell. He’s had the same girlfriend since kindergarten. They grew up together, they got married, and they have three children and a golden retriever named Duke. Scott was never ours to dream about.
KATIE: Jamal is a sharp dresser with a great smile. He seems like he’d be tall and popular, the class president AND the captain of at least one sports team, but then ALSO somehow really nice and not arrogant about his social status.
ADAM: Jamal is employee of the month every month at the car dealership he works at. That sounds really pretty dull until you learn how much commission he makes on all those Nissan Altimas he sells, and suddenly he’s a whole lot cuter.
JEN: Jamal has the best smile/cheek combination. If texting were a thing in the ’90s, Jamal would always text you back. I’m sorry for losing you, Jamal. I didn’t mean to lose you like I meant to lose Alan.
KATIE: I always thought Matt was one of the cutest when I was a preteen but now I’m look, “Look at this fuckin’ face. What is that face.” So SMUG! I probably would still have a small crush on him.
ADAM: Matt is a little baby-faced for me, but I get the appeal. He’d buy you popcorn at a PG-13 movie. He’s probably easy to fall for, but I sense an inflated ego. Also I can’t imagine him ever being able to grow a beard and that’s an issue for me.
JEN: Matt has a unibrow. That’s where his beard went. There’s nothing wrong with that, though. He’s still a cutie.
KATIE: Jason was always seen as the total loser in the pack, and it’s not that I think he looks … GREAT? But I think he looks a lot better than I thought back then. That hair is going to be on his head to the grave. He has interesting glasses. He’s not bad.
ADAM: There’s that movie cliche where the nerdy girl takes off her glasses and lets down her hair, and suddenly she’s beautiful. Jason is that girl. There’s so much potential here, and I want to get in on the ground floor. I wanna lock Jason down early because this fella is going places and I wanna be along for the ride.
JEN: Jason is that guy who you didn’t realize was a stud until he nailed it as Seymour in your high school’s production of Little Shop of Horrors.
KATIE: He has classic, boring features, but there is something a little slimy in the way Tyler is smiling, in a way that I find appealing in spite of myself. Every Tyler I’ve ever known has been the, like, “goofball” among the jocks, and this one seems no exception. Eventually you realize he’s actually just lazy and rude.
ADAM: Yeah, this guy looks like he’d get drunk and be sort of mean to me, then tell me I’m being dramatic when I get upset. Also I don’t trust any man wearing a teal polo.
JEN: Tyler is an honor student who sometimes toilet papers houses. You can tell by his grin. I like it?
KATIE: OK, I had to scroll back up to look at Tyler and Matt, because Dan looks pretty much exactly the same as them. Right?? Are they brothers? Dan is the hottest one though, I think. More modest than Matt, more clever than Tyler. Great brows. We could go shopping to fix the rest.
ADAM: Oh lord, have mercy. Dan is Grade A prime beef and I want to take a BITE. Good hair, great brows, perfect ear shape. I feel like I’d go on one date with Dan and he wouldn’t call me back, and I’d pine for him for the rest of my days.
JEN: I used to think Dan was an astronaut because I refused to wear my glasses as a kid. I’m now realizing that Dan is not, in fact, an astronaut; he’s just a guy wearing a sweatshirt and a turtleneck at the same time. What kind of frigid monster wears a sweatshirt and a turtleneck to the movies? Anyway, he kind of looks like a dude version of Lana del Rey. I’m still into it.
KATIE: Dale is so old. I thought that when I was 12 and playing this game and I think it now, at 27. He could be any age. You could be like, “He’s 39,” and I’d be like, that makes sense. He looks soft-spoken, which is code for boring. He is a boring handsome football player.
ADAM: Dale looks like a d-bag. He probably has kids that he never sees, and he orders his steak well done. I agree about the football thing. He looks like he was an OK player in high school, but he lies and says he was quarterback.
JEN: Dale gives me the same vibes as Matt Damon’s character in 30 Rock, and I’d be willing to bet he grew up to be a pilot who knew every word of Guardians of Ga’Hoole. Definitely an A+ stud with a heart of sweet, boring gold.