Love Column: Stuck in a Sticky Situation


By David Rappe and Tillman Degens

Dear Love Column,

I want to break up with my girlfriend because I like her best friend better than her. The nice part of me says this is a bad situation that I should try to get out of, but I’m still tempted to break up with her and ask her best friend out. I need advice, help!


Conflicted Carl

Dear Carl,

I know exactly how you feel. I’ve been there. I would advise that you break up with your girlfriend immediately. Just kidding, you should try to get at them both. It may be easier for me to decide what you do if you send me a picture of both of them, but their instagram names will also suffice. Because I only know you by a stupid pun and this prompt may or may not have been made up, it could be difficult for you to get back to me, though. In my experience with this situation, and trust me, I often have to chose between a multitude of girls, the best option would be to take the both of them on the most incredible date of their lives. First, you have to address your wardrobe, make sure to be wearing as many name brands as possible to allude that you will be a good provider and that you keep up with today’s styles. I would recommend cutting the sleeves of a sweatshirt into a tank top and wearing a snapback on the very top of your head. Next, you have to rent a nice sports car to show your parents spoil you. For the dinner, you should take her out to the nicest restaurant in Portland and at the end make her pay for it because you spent all your money on clothes and the car. She’ll love how considerate you are and the fact that you don’t fall under traditional first date standards. By the end of this, you will have succeeded because both girls will love you, although they might not show it when they slap you in the face when you tell them they have to pay for the $400 meal.

Works every time 😉


Dear Carl,

I’d like to say we’ve all been there, but I’m pretty sure I’d be lying. Even so, here’s some advice: take both of them out at the same time. You might be thinking, “Where’s this David guy going with this? This sounds like a terrible idea!” This thought will probably go away when you take a look at Tillman’s advice. I know he doesn’t have much experience with this kind of stuff, but don’t worry, I do this all the time. It’s basically just a double date without the other guy. It’s totally normal and cool, and if they say heck no, then your problem’s solved. Now you don’t have to pick between either of them; they both hate your guts. This is a very slim possibility, of course. Chances are they’ll jump at the chance to go on a one and a half date with you. For this kind of thing, I’d advise a Latin-American restaurant with an atmosphere that could only be described as smooth. If you get this far, the rest will be a piece of cake. Pay for them both to make sure they see you as a provider and a gentleman. Compliment the waiter as you give them a massive tip, smiling benevolently as you do so. Make sure both girls can see this generous display of kindness and cash. You’re set now. It’s in the bag. Good luck.

Looking out for your best interests,