All The Men You Date After The Break Up

There’s the guy you meet when you first get back from your post-breakup trip to Europe. He’s 36 and totally your type, older and scruffy and well-dressed and has a quirky sense of humor. He played guitar and liked to paint and lived in Greenwich Village and had a sweet black and white pup named Maggie. He didn’t drink and he smoked cigarettes and he had a good smile and a certain nonchalance. You exchange the typical pre-date flirty banter at first, the kind that gets you excited and gives you butterflies, before setting a date and arranging to meet up for coffee.

He texts you every day, the sweet good morning texts that make you smile to know someone is thinking about you when they first wake up. He sends you pictures of his dog and sound bytes of songs he wrote, and even writes a song for you which he records and sends to you over iMessage. He seems less interested in the conversation and what you have to say, and more interested in trying to get you to say something dirty. His requests for endless selfies start to annoy. They get more aggressive. You meet up for coffee and he doesn’t pay for your cappuccino. You can’t remember your ex ever letting you pay while you were on a date, and it makes you kind of sad.

You actually connect over good conversation, and share some intimate personal stories with each other. He walks you to the subway and you go in for a hug – but he sweetly kisses your cheek in a way that makes you wish you’d have let him actually kiss you. After you descend underground he immediately texts you that he wishes you’d have let him kiss you. You agree, but then think that if a guy can’t even buy you a cup of coffee he doesn’t deserve a kiss. You talk all day though, and even when he goes out of town to Vermont for a few days. He calls you on the phone one night to chat and you keep texting until you’re fed up with the sexual innuendos and inappropriate conversations. It’s too much too soon. You break it off after a week and he responds kindly and respectfully. You wonder how he’s doing from time to time.

There’s the guy who invites you out for drinks in midtown on a Friday night. You normally hate midtown but you know the bar and the drinks are good so you agree. He talks fast and talks a lot and talks mostly about himself. You can never really answer any of his questions before you get cut off. Your answers simply seem to be a conduit through which his stories are given reason to be told out loud. His job is boring, his upbringing is somewhat typical, but he’s from DC and went to college in Pittsburgh so you talk about your common connections to both places. He works in finance and makes sure to let you know about his apartment on Columbus Circle. Despite this, you actually have a fun time on the date. Maybe because you’re three cosmopolitans in and anything can be fun after three cosmos. He goes to the bathroom and leaves you at the bar. Three other guys start talking to you while you wait. He immediately comes over and puts his hand on your back and asks if he can give you a kiss. His mouth tastes like peppermint – he must have planned this moment when he went to the bathroom. You’re kind of turned off by this. You change venues (and switch to Diet Coke) before he walks you to the subway. You kiss again. It’s not great, but you had fun anyways so you agree to a second date.

He reschedules your second date. You’ve dated people who work in finance/work in a finance office yourself, so you know how it goes. Before your second date, you’re feeling a little nervous. Not because you’re overly excited, but because your under-enthusiastic. You don’t really want to go and you’re not super attracted to the guy, but you’ve already committed. He takes you out for oysters in the East Village and then you go to UCB for a terrible third-rate comedy show. You don’t laugh. You’re ready to go home. You don’t really care if you never see him again. This time, he doesn’t walk you to the subway station. He suggests a movie-night-in as your third date, then disappears off the face of the earth and you never hear from him again. You couldn’t care less – actually, you’re relived.

You cry on your walk to the nearest train station – your ex never would have made you walk to the train station by yourself. Hell, your ex always walked you to your front door.

There’s the guy you meet for a drink in your neighborhood – the date who is convenient and nearby and doesn’t require much investment. You have a good time but you’re not super attracted and he comes off as quite cocky. He tells you how much fun he has and how interested he is, and follows up via text to tell you that he “[doesn’t] normally reach out like this, but I wanted to express my interest…”. You have already decided you’re not into him. You don’t follow up.

There’s the guy you meet through mutual friends – this date is kind of a setup. You worry it will make things awkward if it doesn’t work out. Actually, you’re pretty sure it’s not going to work out. You were at a party and told your friend “he’s cute!” after having one too many glasses of chardonnay. Your friend doesn’t realize you are the biggest flirt in the world when you are drunk. Sober you realizes your mistake and confirms that you’re not attracted, but your friend has already put the gears in motion. He asks you out to dinner and you agree to give the guy a chance – what have you got to lose? – only to have the dinner somehow become lunch and a Broadway musical. No, I’m not talking about Off-Broadway; I’m talking about 6th-row center orchestra seats at $200 a pop for the new hit musical Anastasia. Combined with lunch and drinks, you realize this guy spent $500 on a first date. You are extremely flattered and also extremely guilt-ridden; you knew this wasn’t going to turn into a second date.

While you are on the date, you think about how this would’ve been the perfect anniversary date, and it reminds you that in just under a month, you and your ex would have celebrated your one year anniversary.

In the middle of a love song, you start to tear up. You glance over at your date and hope he doesn’t notice. You part ways and hear from him sporadically but kind of avoid making plans. You hope that it won’t be awkward next time you go out with friends.

There’s the guy who flakes out while you are in the middle of getting ready for your date – offering to meet you two hours later instead of the original time because of a work party. You tell him you’re booked solid for the next few weeks but best of luck. You think about how you used to get mad at your ex for being late all the time. You wonder if you were too harsh.

There’s the extremely boring guy who talks about all of his travels and bro friends and eating pot brownies with his sister at a concert. He brags about his “amazing” job (in finance, of course) and his “amazing” apartment in Williamsburg (gag), then asks you to split the check at dinner. You decide he’s a walking cliche and wonder why you keep giving finance guys a shot. You cry again on your way to the subway, this time the tears falling even harder. Your ex would never have asked you to split the check. When he texts you twice, you decide not to ghost and instead tell him that you’re not “feeling it” and that in future if he hopes another girl will “feel it” he’ll man up and pay for the first date. You block his number and delete your message thread.

There’s the last guy you’ll date before you decide to take a break. He’s exactly your type – tall, dark, seemingly mature, and handsome – in fact, incredibly handsome. You’re smitten and the chemistry is electric. He’s 38 and twice-divorced and has two kids. “He’s everything your ex was not,” a friend will tell you. You know this will never work and yet…you’ve never been so immediately attracted to someone. Or maybe you have and it’s just been a while. You want to ride it out. He takes you to the Rubin Museum and then out for Thai food once you both realize it’s 9:30pm. On the walk home, you make out on the street before finding a more secluded spot in Union Square Park. It’s 1am. You go home. You already have a second date lined up for the next morning before he has to leave the following night to go see his kids in Philly. You ignore the last bit. He’s sweet and consistent and texts you every day and even calls, but you don’t get to see him much. He spends a lot of his weekends going to visit his kids. He tells you how much he likes you, how he is incredibly attracted to both your looks and your personality, how he wants to “take you off the market.” He talks about a future, plans outings to the beach, the Highline, Chelsea Market, sushi crawls. Yet you’ve been “seeing each other” for a month and have only been on three dates; you know that he’ll never have the time to do it. The reality of the situation smacks you like a ton of bricks. You don’t even LIKE kids.

You break it off with him and never hear back. You realize he was never worth it anyways, and you’re not all that sad. Somehow, this guy made you miss your ex the most.

There’s the guy you’ll see walking up the other side of the street as you’re walking down, a few quick blocks away from your apartment. You do a double take – your heart literally stops. Your hands start shaking. It’s your ex. You think he sees you but you’re not sure. You turn the corner and keep walking to your apartment, but you wish you could go up to him and tell him how much you’ve missed him. You wish you could go up and tell him you wish things had worked out differently. You wish you could tell him that despite your problems, he set the standard for a boyfriend pretty high; you wish you could tell him that despite everything, you still love him.