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Mallory Schlossberg is a writer and performer in New York City. She lives in Brooklyn, and blogs at You can follow her on twitter @ malloryschloss.

Me: I have to go after brunch. I have a lot to do. I have to work on my proposal, and I have to read a bunch of books for it.

Him: That makes sense. To compare it to?

Me: Yeah. I mean, but I like the book I’m reading now.

Him: Yeah.

Me: I’ve never had brunch before.

Him: What?

Me: I usually work on the weekends. And I never had somebody to have brunch with before.

Him: Well, baby, you’re havin’ brunch today!

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Him: So…what do you like to do in the summers?

Me: Um. . . I don’t know. I mean, last summer I worked on my show a lot. I did it twice.

Him: You don’t like, go to the beach?

Me: Well, I don’t know. The summer to me is just an extension of the rest of the year, except I’m wearing shorts. And I never really had anyone to go with. When I have free time, I take on projects, classes. I work on my show.

Him: I love going to the beach. I went to Fort Tilden last year.

Me: That’s the nude beach.

Him:  It is?

Me: Oh! That’s Vampire Weekend.

Him: It is?

Me: Yeah. I was supposed to see them in concert a few years ago, but I got the flu.

Him: They describe themselves as Upper West Side Soweto.

Me: Huh?

Him: Do you know what that is?

Me: No.

Him: It’s South African music. Upper West Side South African. That’s disgusting.

Me: Um, well, I like their music.

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 Him: So, there’s something that’s been bothering me.

Me: Yeah?

Him: All you ever talk about is work.

Me: What do you mean?

Him: Like. What your’e working on. Your proposal. Your show. Improv.  It’s like, all you do.

Me:  I mean… I don’t get paid to do what I love. So it doesn’t feel like work. And it’s what I love. It’s what I like to talk about.

Him: But I mean, earlier. You told me you were reading a book for your proposal. Why don’t you instead tell me what the book is about.

Me: Okay. It’s called “My Boyfriend Wrote A Book About Me.” It’s about this woman whose boyfriend wrote a book about her. And then she tells stories about her life post-break up. It’s funny.

Him: See! That’s a conversation! I’m reading a book (I tune out.)

Me: Oh. Wow. Really?

Him: Yeah. I’m enjoying it.

Me: I don’t always talk about work. I work a lot. But it’s not work. I’m bothered that you said that.

Him: Well, I did. And I was really worried about this, but then I saw you and I knew everything was going to be fine.

Me: I love what I do.

Him: And that’s great – but listen. I have passions, too. I moonlight as a video game designer.

Me:  I’m not here in New York to teach SAT prep. And you have to realize you met me at a weird time because of the holidays. It’s going to be different soon – I won’t be around as much. I’m a really busy person.

Him: But you do work a lot. And I don’t want it to be – you come home, I come home, we have dinner, and then we have sex. I mean, sex is great, but I’m not going to remember sex. I am going to remember a picnic. I like picnics. Olives, bread. I want to make memories. Go to the park. Go to that movie theater in Dumbo and get a six pack.

Me: I need to get a bike. Want to help me get one?

Him: YES! See, I love that you asked me that.

Me: I also need to get my library card. Wanna come with me?

Him: YES! See, I like this. Doing stuff together.

Me: I’ve never really had someone to do these things with. So I guess I don’t know what I like to do. Besides comedy and art stuff. I’m just not used to this sort of…

Him: Mallory. You’re writing a book about dating OkCupid boys. Now your’e dating a man. Things are different.

Me: I want to go dancing.

Him: Let’s go. Let me get your coat.

Me: (I see someone I know) Hi! How are you! (back to him) That’s someone I know from improv.

Him: Oh. Okay… Cool.

Me: I still don’t like what you said before.

Him: What? I was worried about something, and we talked about it, and I feel so much better about it now. Let’s go. (he takes out his iPhone) I want to take a picture of us and send it to my mom. (Click) Ah, came out too dark.


photos, tri vo

guest edited by samuel lindeman.




photos by erwin caluya


So, I was wondering if you know – how do you know when a guy wants you to stay?

A week ago I went into the city to hang out with this guy.  He was really cute and nice, with a sexy Spanish accent.  I get to his place and we talk for a while and we seem to be hitting it off.  We then move it to the bedroom and do the dirty – and it was fun.  Then we take a shower and jump back into bed and watch tv.  This is where the awkward part comes – we watch a movie and then another tv show and then he gets hungry and makes a salad and opens a bottle of wine. 

You think “this all sounds great,” but the whole time I’m wondering when I should leave.  The stupid guy that I am, I don’t leave after the food and stay to watch more tv.  By now it’s 12:30 and he’s getting tired and I have no clue if he wants me to stay the night or not.  I give him a back rub.

Then he says, “I’m assuming you want to sleep over.”

I respond, “Only if you want me to.”  He gets really silent.  Then I ask him again and he responds, not really – he has to wake up early.  I knew that I had over-stayed my welcome and to make matters worse the area he lived in had no taxis around.  Finally he called me a taxi, but I wound up missing my last train home and wound up walking around the freezing cold in Manhattan for 7 hours.

What should I do to avoid this in the future?

Thank you, Jerk


Dear N.,

Thanks for your letter.  You sound like maybe you’re new to online hook-ups.  There’s a certain amount of etiquette involved, but that etiquette is, unfortunately, different for every person.   As a general rule of thumb, if it’s a hook-up and not a date then you should fully expect to leave shortly after the sex happens.

This is not to excuse any amount of poor behavior on the part of your Spanish accented friend.   Unfortunately, guys have a way of being super charming with a new conquest right up until the point of orgasm.  After the deed is done, however, reality comes crashing back in and you’re left there in your own home with a relative stranger that seems to want to eat all your salad and watch West Wing re-runs until 2 in the morning.

Next time, explain your situation before you go over to the guy’s house.  Let him know you live outside the city, and if he wants you to come over he’ll have to let you stay the night.  If he says no, then at least you know what you’re dealing with -a guy who wants to bone you and say goodbye shortly afterward.

If I may say so – it does sound like you might be looking for a date, instead of a hook-up.  In which case, I think you’d be far better off using websites like OkCupid rather than Craigslist or Grindr.  Just a thought.

Be honest about your intentions and you can’t go wrong.


P.S.  Next time you’re walking around freezing in Manhattan, go to Penn Station.  It’s warm in there and you can pretend you’re waiting for a train to leave.