Ask Caroline: My Girlfriend Recently Got a Large Inheritance of Money … +

Have you ever wanted therapy but can’t afford it? Well, this advice column definitely can’t replace therapy, but I’ll try my best. 

I’ll answer all your burning questions about life, love, Bushwick and organized religion. Thank you to our readers who sent in a ton of honest questions. I’ve plucked only the ones I’m qualified to answer. 

Dear Caroline: My girlfriend got a large inheritance of money and told me she wants to take us on a fancy vacation with it. When we were researching places to go, she said I can send her whatever amount of money I want for the vacation. I’m confused because she said she was going to pay for it, so what should I do?

Okay, wow, obsessed with this story. The drama of inheriting a whole lot of money is truly incredible. But … lest we forget … “More money, more problems.”

I’m picturing “Knives Out.” Your girlfriend is Ana de Armas and inherited all this money and tons of people are pissed at her, but she doesn’t care. She’s in a massive mansion now. She calls you up and says, “Babe. We’re going to Paris.”

Why on earth would she then ask you to pay some amount? There are two reasons. 

1. She wants to make you feel like you are contributing to the vacation. There is a level of guilt when someone pays for absolutely everything. It’s like when someone takes you out to dinner and you make sure to not order the $78 steak. At least that’s what I do. Maybe she senses that in you and wants to let you be totally guilt free on the trip.

2. She is suddenly realizing maybe she shouldn’t spend all of this money just on one trip. It’s easy to go crazy when you first get money. When I got my first job, I spent the first three paychecks on clothes. Then I realized, oh God, I have to actually pay rent. Maybe she’s getting her ‘oh God’ moment. To be honest, your girlfriend is super relatable. She dreams big, but when it comes down to it, she might be realizing she still needs to feed herself for the next year. She doesn’t want to tell you to pay for half of the vacation, because that would be way too much and she did say she would treat you both. But, this is her way of hinting at – maybe if you could pitch in that would be great.

Either way, you have to talk to her. Be honest with her. Say you’re a little confused. If you don’t have the money, let her know. Maybe going on a massive trip with her inheritance money isn’t the best idea! (Although I pray you do. But please make sure you don’t go somewhere boring like Aruba.) 

Dear Caroline: I confessed to a crush and they haven’t messaged me back since, what should I do?

Okay, thank God: a lower stakes question than the first one. Firstly, you are brave and amazing. I have never once confessed to a crush in my life. I have only made tiny, tiny hints at them until either nothing happens or they make the first move.

You are awesome and a catch if you are telling a crush you like them! That’s everyone’s dream.

It seems like maybe this isn’t 100% reciprocated, which stinks, I know. To confirm, I would send them a follow-up asking them on a date. They have to answer! If they say no, boom, you can officially move on. If they say yes, woohoo! Take them out for a big steak dinner.

Dear Caroline: How do I stay up to date on fashion trends?

This has been plaguing me since the dawn of time. Guess what? It’s actually impossible to stay up to date. With micro-trends and fast fashion, what’s popular is always changing. You finally find out about a trend three weeks late, buy it, and then wear it for one month before it’s gauche. You’re cooler than that. I’ve been wearing gaucho pants and Bobby Jack tees, and I love it. You don’t have to be bold. You can take inspiration from fashion trends throughout the years, not just what is hot today. Figure out what you love from over the years, and curate a staple wardrobe that won’t go out of style in two days. 

Caroline Cianci is a a stand-up comedian and comedy writer living in Bushwick. Caroline also runs a monthly comedy show in Bushwick called Last Drop Comedy. “You should come sometime!” she says.

*If you have a question for Caroline, comment it below or respond on Instagram!

Featured image: Photo by John Guccione from Pexels.

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