The Single Woman’s Dating Playbook: Helping A Reader Plan His Date

The Single Woman's Dating Playbook: Helping A Reader Plan His Date

I have peaked. All my wildest dreams have come true. That’s right you guys, someone actually contracted me to PLAN A DATE FOR THEM. Okay, so I understand that the word “contracted” may connote some sort of payment, which I can guarantee is not the case. But you know what – the god damn request is payment enough.

My heart has never fluttered quite like it did two weeks ago, when a reader slid into my DM’s with one simple, life changing question. “CMV – Can you help me plan a date?”

Oh my god.

“YES!” I screamed through the phone 3 seconds after I received the request. The near immediate response certainly did nothing for my reputation as a super chill/hot/cool girl – but I was just so frickin excited! (Plus, that whole chill/hot/cool girl ship sailed about 2 days into my being published on the site).

Once I collected myself I responded to my new best friend with the following:

1) Tell me about yourself! Are you confident on first dates? Shy? Good at small talk or better when you’re doing an activity? Recently out of a relationship?

2) Tell me about the person. How did you meet, what do you know about them, what is your banter like?

3) Where do you live? Give me some logistics: is the date after work, is it a brunch date, do you live far from each other etc.

Honestly, I should have just made a questionnaire.

For two whole hours I waited in anticipation. My friend, let’s call him Brandon, had seen the message – so why hadn’t he responded?! Did I scare him away?? That’s when, to my sheer delight, he replied, “Check your e-mail”.

Brandon, god bless his soul, answered all of my questions and more. He has given me permission to publish this column, including quotes, with the understanding that he will be kept anonymous. Of course, that’s not a problem – I’m a god damn vault. Although, it’s truly a shame the world will never know who the real Brandon is. Let me tell you, the kids a catch. That being said, I’m not sure how much longer he’ll be on the market.

The below is a new entry into the Single Woman’s Dating Playbook crafted specifically for Brandon. As always, however, these plays are for everyone. They’re for the collective Single Squad. They’re for the Single Woman inside us all. Take this play and make it your own – if it worked for Brandon it can certainly work for you.

Do Your Research

I asked Brandon about himself first. Here’s what he said (part of what he said, dude gave me a LOT of info):

I’m a 24-year old living in Philly. IDK if you know Philly but I live in Fishtown. It’s pretty cool around here, like a ton to do etc. I’m an engineer and spend most of my day around people I don’t like that much so I try to get out as much as I can….I broke up with my girl last year and haven’t really met anyone for the past year. I went to a big school for college and did my fair share of partying. Since then I moved to Philly and worked hard to meet new people, so I’m pretty social. Not shy, good at talking to girls. Ever since I studied abroad in Europe I travel as much as I can, just got back from a solo trip to Indonesia. Otherwise I do normal stuff like go to the gym and bars.

I imagine Brandon as your traditional college kid that got the jungle juice out of his system by senior year, and upon graduating hit the road looking to start fresh. He’s smart (the engineering degree) and has a robust social life which he created postgrad, an impressive feat. He studied abroad in college (I’m guessing Spain) and during what I’m sure was a beer fueled Americanized 6 months of spending his parents money, he actually came away with a better understanding of the world that made him a little more self-aware. So much so, that he has made it a habit of frequently traveling alone. Brandon’s got a soft side.

Here’s what he said about the date:

Like I said I broke up with my girl a year ago and have been single ever since. I’ve dated on and off, but always try to be upfront with girls that I’m not looking for something serious. I was really trying to get settled in my new living situation/job etc. Now I’m looking for something more serious.

Okay, so Brandon isn’t too rusty on the dating front. We won’t have to ease him in like someone who’s back in the game after 3 years of self-love. That’s helpful. Now tell me about the girl, dammit.

I met this girl (and this is the reason I’m writing) through a friend of a friend. She’s really cool and super outgoing. Like she has an awesome personality and she’s really pretty so my buddies and I all love hanging out with her. She really seems like she has her life together. She works in marketing and is 23 so is basically working all the time. She’s super funny, on our first date I was laughing the whole time.

Let’s call Brandon’s date Sarah. Sarah has her shit together, which Brandon likes, but it’s also something new for him. He’s kind of enamored by it all. She’s one of those girls that is running around constantly, endearing because of her confidence, and seems to be taking her 20’s by the balls. Good for you Sarah.

We’ve gone out on 3 dates and she came over to my place once to watch a movie and ended up staying over. We have another date planned for this week. Initially I suggested going back to the place we went on our first date because it’s a nice bar and we both liked it, but now I’m thinking that may be lame. Through her texts the past few days she seems more distant and like less excited then she usually is. Honestly I’m worried she’s losing interest.

Ah Ha! There it is Brandon. It was a long road but we got there. I’m going to take a leap here, because this is my column and I’m feeling wild and say that I think you misspoke slightly. After three dates and a sleepover you’re not afraid she’s losing interest in you, you’re afraid she’s getting bored. Now, those may sound the same, but they’re not. If she was losing interest, it would mean she realized she’s not that into you. We both know she’s into you because a) sleepover b) 3 dates c) hasn’t canceled 4th date.

What could potentially be happening, and what I think is the root of your anxiety, is that she is getting bored of you. You’re afraid she’s getting bored of doing the same vodka soda, meet-me-at-happy-hour dance, so much so that things may fizzle out. And that, my friend, is why you came to me. We can fix this.

Plan Your Play

Throughout our email exchange I also learned that the date was set for a Thursday night and the two lovers live relatively close to each other in Fishtown. After I digested Brandon’s email, and thought about it for a bit, I planned my play. Well, technically, I planned his play. The below is my response to Brandon. (I’m leaving out the part about how brave it was for him to e-mail and how much I love him because that was a special moment just for us).

My dude. As you know, I have never lived in Philly so planning a date is going to be hard. That being said, I don’t know if you know this, but I like a challenge.

First things first, I’m going to give it to you straight. If her texting has been distant, she’s wondering if the juice is worth the squeeze. She’s a busy girl and committing to dating someone is, well just that, a commitment. It seems like she’s got a few guys that will buy her vodka sodas and laugh at her jokes, so if dating you seems, for lack of a better word, repetitious, that’s probably why she’s become distant. She’s managing her time.

THAT BEING SAID YOU’RE STILL IN THIS. You’re right to say she’s probably not going to want to go to the same place that you went on your first date. Also, this date is after work, and she works hard, so I can guarantee she’s going to want a drink. I certainly wouldn’t pull a 180 and do anything crazy like plan a night hike – her life is exhausting enough.

If I was her, I’d want a date that is both stimulating and relaxing. It’s got to be worth her time (not just another trip to another bar) but not take so much effort and commitment that she’s fatigued by the whole thing before she gets there. I know that’s a tall order – but I’m here to help. See the below date, adjust as needed, and PLEASE GOD tell me how it goes.

Shoot Your Shot

Here’s where, like a psychopath, I presented Brandon with his very own date for which I did FAR too much research. Let’s call it “The Brandon.”

After work at 7:00 PM meet at The Root on Frankford.

My sources say it’s a trendy tapas bar. I just looked at the menu and I would love for you to get the Crispy Potatoes in my honor. DON’T do dinner here, just sit at the bar and order some snacks and 1 drink. Pace yourself. The place is pretty, it’s trendy, and I’m about 93% sure she’ll like it. It will set a nice mood for the evening, like you take her seriously and she’s worth taking to a fancy-ish spot.

After you wine and dine and the waiter asks if you want a second drink, turn to her and say, “Want to get out of here? Let’s go somewhere a little more relaxed”. (I mean, don’t like memorize that, but say something along those lines).

Walk down the street to Frankford Hall

This is a German place with liter beers, Ping-Pong, and lots of outdoor heating lamps (I checked). They also have giant pretzels, which you should order because you’re young and you’re on a date with a pretty girl and by now she’s really hungry because tapas are tiny. Drink your beers, play some Ping-Pong, and make her laugh. I’d stick to one beer because the night ain’t over.

Once you tire of a loud bar and have finished your drinks, ask her if she’d want to come back to your place. If she doesn’t, be a gentleman and get her in an Uber. If she does, however, suggest you swing by the liquor store on the way home. There’s a wine and spirits store a few blocks away under the Acme. Again, I checked.

***Side note, I’m realizing now you haven’t eaten that much food. On your way to the liquor store, if you’re hungry, stop by the taco truck called Calle Del Sabor. They’re insane, my sources tell me.

Here’s when you’re going to tell Sarah about your time in Europe where you first learned about mulled wine. The perfect holiday cocktail for freezing European winters. “Hey!” you might say, “This is kind of nerdy but let’s make mulled wine! It’s so cold out.”

This part sounds complicated, but it’s actually so very easy. You need dry red wine, a little bit of brandy (optional, but not really optional), honey, cinnamon, and an orange. This week at the store buy the non-alcoholic ingredients and on your date purchase the liquor.

Head back to your place, pour the wine (whole bottle), brandy (1/4 cup or to taste if you’re wild), and a good squeeze of the honey into a pot. Put the pot on the oven to simmer (not boil or you’ll boil off the alcohol) for 15 minutes. Once it’s done throw some cinnamon and orange slices in that thing, pour it in two mugs, and sit on your couch and cuddle. You know you want to. I give you permission to cuddle.

It’s freezing outside, you’ve got a hot cup of alcohol in your lap, a pretty girl who’s into you on your couch, and some very good holiday vibes. She’ll love it.

And then, my friend, I think you can take it from there.

All my best,


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Life is messy, let's get dirty.

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