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News / Sex & Dating

Meet The Undateables: Alyssa and Billy

Each week, we take two New Yorkers who swear they're totally undateable, and put our matchmaking skills to the test. Afterward, we find out what went well on their date, and what went horribly, horribly wrong.

Photograph: Kelsey Dubinsky


Why they're single:
Alyssa: She’s picky and has trouble finding someone with a good sense of humor.
Billy: He has a busy schedule, and it takes more than just a beautiful woman to turn his head

Ideal date:
Alyssa: Happy hour at a bar, or something very noncommittal.
Billy: A picnic in Central Park


First impression
Alyssa: “I didn’t want to be that girl who’s late, and I was trying really hard, but I was about three minutes late. He stood up, and we hugged. He was really nice and charming.”
“She was about five minutes late, which annoyed the shit out of me. As soon as she walked into the room, I knew she wasn’t the girl for me. She didn’t have the goods.”

Alyssa: “He’s an actor, and that’s totally uncharted territory for me. I like a really stable job in a significant other. But the conversation was very friendly. He did a lot of the talking.”
“Whether I was attracted to her or not, I still had to sit there for two hours and be a gentleman. We had a nice conversation. She complimented me many times.”

Awkward Moment
Alyssa: “A couple of times he told me not to be nervous. I wasn’t nervous, but that made me second-guess myself and get in my head. And then the conversation stalled.”
“She ordered her filet mignon well done. The waiter just looked at me, and I looked at the waiter. I was like, ‘Live your life, but this is not Outback Steakhouse, girl.’ ”

Alyssa: “We got a little ice cream afterward, which was awesome. We both gabbed about the fact that we really respect a place that will give you a macaron with your ice cream.”
“I was trying to be nice and end the date, but the waiter was like, ‘Do you want some ice cream?’ and she was like, ‘Yay! Ice cream!’ So that was another 20 minutes.”

Alyssa: ♥♥♥ “We left the restaurant, walked to the subway and said goodbye. I’m really glad that I met him; he was really interesting and cool. But I got more of a friend vibe.”
Billy:  “There was nothing drawing me in. She was very sweet, always smiling, always bubbly. But I feel like I took two hours of my time and kind of just burned it.”

Our daters went to Greenwich Steakhouse (62 Greenwich Ave, 212-553-5000)

RECOMMENDED: See more Undateables

Want to be set up on a free blind date? Email



aj j

idk i had a good laugh about it. Like I can imagine him as a sitcom character lol. This does not mean I like him; he kinda seems mean and dramatic haha


Lolllllll!!!! This is my ex-boyfriend. Not surprised AT ALL.

aj j

@aleahopesheldon  omg please tell us more. ps on his twitter he claims he was misquoted. Thoughts?

Meghan l

Oh Billy! what does it feel to have ruined your own "promising career/love life" ? Can you imagine? every person you'll ever come across for the rest of your life finding out about how low- life you are??

You [should] may get a visa to go to Canada. I'm sure your mother regretted not switching you at birth

Lisa W

Alyssa is adorable and sweet. I feel bad for her that she wasted two hours on this creep. At least she got a good steak out of it, because he clearly didn't bring the beef. "He did a lot of the talking..." About himself I'm sure. She qualifies for sainthood for listening to him prattle on. Buh- bye Billy!

Alyssa, good things are ahead for you.

Billy, enjoy making out with yourself.

Pernilla P

Well, Billy was right about one thing - he really is undateable. Suffering from Trump-complex, expecting everything and everyone around him to look and act like his self-absorbed unreachable dream scenario at every turn. 
What a perfect example of a grade A douchebag.

Benjamin G

I think he is just GAY, doesn't know it yet, so doing these stupid dates...

Rose F

He is a spoiled last born. He will do anything to get attention. I think any "nervousness" she felt was her gut telling her to leave. Sorry you had to waste two hours with this man-child. Silly Billy don't trash talk a woman. Be a gentleman. Is acting your true purpose or is it just for ego? I have a funny feeling we've all been set up. Kinda like the news I read everyday. I feel bad if she is reading what he said.  She was up and positive and he was swimming in his own baby food ego stinking poo..

Renee S

ouch.  why so harsh Billy?  You knew already she didn't have the "goods"?  what does that even mean?  how did you know this?  simply because she was late?  5 minutes?  Give me a break.  

Next time don't force yourself to "waste" 2 hours of your life when you've decided in the first 10 seconds of meeting someone that they are not a match.  You lead that person on and make them think you are enjoying yourself as much as they are.  Oh but wait... maybe you were just "acting"?  

aj j

@Renee S  okay so what do you suggest he should have done or anyone should do in that situation? 

Randy P

Even at the most difficult moments my wife of twenty-three years and I have had, reading this makes me so glad that I'm married.

Stevie R

“She was about five minutes late, which annoyed the shit out of me. As soon as she walked into the room, I knew she wasn’t the girl for me. She didn’t have the goods.” 

He has no idea how many times casting directors have had the exact same thought about him.

He'll be happy when he stops casting his girlfriend and actually gives someone more than 5 seconds to "have the goods". Or be alone forever because he's a superficial douche, either way. 

No one with this lack of interest, curiosity, or empathy is a good artist, so good luck, kid. 

Kira M

So...I kinda know this guy. I met him like 1.5 times on a gig and we spoke maybe eight words to each other. A little while later, he asked me out via FB messenger. No introduction, no pretense, just "Coffee sometime?"

Although I kinda respected his boldness, I didn't even respond because:

(a) As mentioned, I barely knew him. In fact, I had to message one of our mutual friends (the woman who had hired us for said gig) so I could remember how we even "knew" each other in the first place. (Her response: he's "kind of needy.")

(b) He's six years younger than me, which is more like 10 when you consider how much more slowly men mature than women, and

(c) Once I actually figured out who he was and gave his FB profile a once-over, I thought he gave off a massively self-absorbed fuckboy vibe. Clearly my instincts were spot on. 😂😂

On behalf of actual professional actors everywhere, I apologize that this guy is out there giving us a bad rap. He does not represent the majority of us--then again, the majority of us are females or gay men.

And contrary to popular belief among the acting community, if you want a heterosexual actress to like you, it's NOT enough to simply exist and be straight.

More tales of Billy's fuckery can be found at:

Kristy M

Wow he was almost attractive, Now all I see is an uber-douche. #don'tdateactors

Kira M

@Kristy M PLEASE I BEG OF YOU don't judge the entire acting community by this one douche. Word travels fast in our circles, and I've already heard from like 10 people who had similar experiences. Trust me, he does NOT represent us, and there is a veritable sea of people who are more talented, better looking, and actually good people whose existence will put him at the bottom of the barrel very quickly. He'll become a textbook bitter community theatre cliche in about a year and a half, I guarantee it.

Stevie R

@Kristy M Working actors have heart and empathy and love. Also usually intelligent and curious. Pretty boys who think they are actors but aren't actually working or creating are douche bags that give actors a bad name. 

Kira M

@Stevie R @Kristy M exactly. If you want to date an actor, date an actor who's working. Not just someone who says he's an actor.

By the way, when I say "someone who's working," I don't necessarily mean someone who's getting paid. This business is difficult, everybody knows that. But you don't need someone to give you a job to be a "working actor" or performer. Write something with your friends. Do a cabaret. Take a class. Do a play reading. Work in community theatre if your union status allows. Direct something. Hell, do background work--there's no shame in that. If you live in NYC, finding creative things to work on isn't hard. Being a "working actor" isn't about how well-known you are or how much you get paid. It's about how much you want to make stuff.

Stevie R

@Kira M @Stevie R @Kristy M PREACH. Yes, this. I work a pretty legit office job and I'm still an actor/comedian. I love dating other actors/comedians. They aren't terrible. 

The ones who say they are actors but don't delight and are there for the ego stroking and notoriety and superficiality in doing it are gross. 

The ones who will do it no matter what (even when we aren't getting paid or it's in a gross basement at 8pm on a Wednesday and our ego doesn't stop us) and are doing it because it makes us happy and gives us a voice are awesome humans. 

Kira M

@Stevie R @Kira M @Kristy M FACT. Some of the most talented and professional performers I have ever met are the ones who have full-time "regular" jobs and just do community theatre on the side. Professionalism is 90% attitude.

Kristy M

@Kira M @Stevie R @Kristy M Aww guys, I'm sorry. It was a flippant comment because at one time I considered myself an actor so it was a little tongue in cheek joke about my personal experience dating people in that field. I  have since moved on to writing and production because, to be frank, it IS difficult to weed out the genuine and sincere people with a strong work ethic from the narcissists in that profession. Even the girl in this article found him to be charming and gracious and had no idea he was such a scumbag.  Now she does. And you are right, I have a lot of respect for talented and dedicated working actors, and you are also right in that the ones who give the profession a bad rap are usually 99% ego and only 1% talent. 

Stevie R

@Kristy M @Kira M @Stevie R Not even mad about it. Just hate when people think this is limited to one industry. Except finance. All guys in finance are like this (jkjkjkjkjkjkjk).

Ana L

That guy is really not a nice guy. Hes very moody and perhaps workaholic. ?. Hes not fun to be with i guess.

Chris L

Well done fillet mignon?

A tiny bit of bovine-related ozone was sacrificed for a terrible meal.

This dude got heated with a date because she was an entire *five* minutes late? Who could even be bothered to give a shit about that?!

Ana L

He was a really scary guy i guest.?.

Jack M

This guy, with a puffed-up sense of himself, thinks he's god's gift. But he truly is really an ugly son-of-a-bitch inside, regardless of his pulchritude which, as we all know, is fleeting. I believe this guy is a closet case who hates women and he should lose the pretense of even liking them or wanting to interact with them. And for that reason, he is a prime prick, a faker,  who should be avoided at all costs. Ladies, get your steaks and just desserts some other way. 

Timothy O

Billy looks at the waiter, the waiter looks at Billy...3 minutes pass as they gaze deep into each other's eyes...Alyssa coughs to interrupt their moment... "Think that steak should be crispy by now boys" she says with a smile.

Kira M

@Timothy O You just wrote the gay porn movie I never knew I needed.

Jay M

This guy knows that he was talking to a reporter, right? Like, he knew this would be printed for people to read?

Kirby C

Billy... your'e a douche.  Thats what NYC has to offer.

Sean D

Never date a girl who's idea of a first date is "happy hour", but I guess that's what you get from the dating pool in NYC. 


@Sean D THAT'S your takeaway from this?
You're a bad person and you should feel bad.

Sean D

@M M @Sean D Boohoo did I hurt your feelings because I didn't side with the oppressed woman? 

Al L

Maybe Billy is single because he can't date himself... or his assumedly rare (+) filet mignon. Also, isn't Billy a child's name?

Alyssa, stick to Williams or Benjamins and just let Billy "love" himself.

Cameron B


I want the internet to drag him.

Rosie B

Eeew now I know why billy is single ...what a total asswipe👎🏻 ...ladies run run run

Kels C

I know Alyssa from college and she's a sweetheart. This asshole needs to get a better grasp on reality

Alexander C

Billy will play the role of a corpse on Law & Order (which is no longer in production) and go on to have an exciting career as a Civil War Reenactor.

Ray L

@Alexander C He'll wind up back in his home town working in an insurance office or (worse) teaching a drama class to middle schoolers, and sell himself to local theater as a "New York Actor", meaning he'll get the gigs the guys who've worked their butts off locally should get.

Kira M

@Ray L @Alexander C he's from Westchester County (which is just north NYC), and word spreads SO FAST here. Trust me, we don't want him either. Maybe a few community theaters will put up with him if they need somebody, but honestly I wouldn't be surprised if some places have blacklisted him already.

Allison B

I feel like she was trying to be a good person and be positive about a bad experience, like I was when I did one of these and the guy was a total douche. 

pat s

What a douche-nozzle that wanna be "hacktor" Billy is...could such a loser be so cluelessly in love with himself? I haven't seen that unwarranted and inflated an ego since Trump. She could do much, much better-he's truly an asshat going nowhere fast. Gag.


Billy will abandon his acting career to go work for Martin Shrekli. 

Alyssa will twist her knee in a Soul Cycle class and end up marrying her orthopedic surgeon;  20 years her senior.  They will summer in the Hamptons.  


I'm not sure whether Billy is just a total jackass or actually a gay guy desperately trying to pass. What kind of straight man says, "this is not Outback Steakhouse, girl” or even thinks it? Next time try the waiter, he seems more your speed.

aj j

@AC W  oh come on' youre gonna assume someone's orientation just by that comment? Some would say that's homophobic. I dont wanna defend him but it could have been a quote tacked on or manipulated by the writer idk. Many people want to look progresssive~and accepting but then say shit like this.

Jesus L

shes single because she buys her clothes at the 99 cents store -- honey you might wanna try a little harder to impress: jus saying !