Ask A Hottie Vol. 8: I'm Dating My Daughter's 20-Year-Old Friend, Should I Tell

Welcome to Ask A Hottie, a weekly column in which Break has decided to let a girl who 1. Is writing this at the utmost last minute on a Sunday night because she’s a terrible procrastinator, and 2. Might be sort of drunk right now.

But on the bright side, I colored my hair. ‘Tis no longer purple, it’s now pink:

Do you have a question for our resident pink-haired…whatever she is? Email!


Q: “Abby” and my daughter have been friends her since senior year of high school, and they lived together during their freshman year of college. I have always been friendly towards Abby, but in an appropriate way. She is a pretty girl but I never thought about it until recently because I assumed that:

1. She would never be interested in me because I am 37 and she is 20

2. That sort of relationship would be inappropriate due to our ages and the fact that she is friends with my daughter

About two months ago Abby came to visit my daughter and spend the weekend with us. That Friday night I came home late from work and found that Abby and my daughter had been drinking out of my liquor cabinet. I told them to go to bed, sleep off the liquor and that we would talk about it in the morning.

I stayed up for a couple more hours and Abby came downstairs. She apologized for taking the booze, though she was still pretty drunk, and our conversation eventually led to her admitting that she had a crush on me ever since she came to our house for the first time back in high school. Abby then tried to kiss me, but I told her this was a bad idea and to go back to bed.

But what she said bugged me the rest of the night, so in the morning I asked if we could talk about what she said. I felt like our conversation ended on a high note, and that the story was essentially over.

Except…I couldn’t stop thinking about it. I reached out to Abby on Facebook and asked if she wanted to go to dinner with me one night. She said yes, and we’ve been quietly dating for the past month. She’s smart, fun and we have a lot in common.

I am pretty sure my daughter does not know this is going on, but I don’t know if we should tell her or not, or if this is even appropriate in the first place?

A: Because I know every single person reading this is going to say the same thing…

…here’s a high five for bangin’ a 20-year-old college girl. But wait!

Here’s another high five for basically living out the plot to thousands of porn movies.

Unfortunately for you, that’s where the congratulations end and the spanking begins: Bro, WHAT THE FUCK ARE YOU DOING.

It’d be one thing if your daughter knew and gave this fucked up relationship her blessing, but she didn’t. It’d be one thing if this girl wasn’t your daughter’s close friend, but she is. It’d be one thing if you didn’t literally say “this was a bad idea” in the middle of your recount of what happened, but you did, and even went on to ask if this was appropriate. Dude you know the answer to that question already, you’re just looking for validation because you don’t want to stop.

And the thing is, I can’t make you stop. I don’t care if you fuck Abby or if you fuck Abby and your daughter together in the 2017’s most uncomfortable threesome. You and Abby are both consenting adults of legal age, but take a minute to think about it like this:

Your daughter says she’s bringing her new boyfriend over for dinner one night. You didn’t know she even had a boyfriend, she won’t give you any details and says that you have to meet him before she says anything. Lo and behold, SURPRISE! Your daughter’s brand spankin’ new boyfriend is your good friend from work who happens to be 38 and divorced. Scale of one through ten, how thrilled are you?

If your answer was “zero,” you’re a dirty fucking liar because that’s not low enough. Now you learn that she’s been dating this dude for two months behind your back, and neither she nor your friend had the balls to tell you to your face — NOW how thrilled are you?

Yeah, that’s what I thought. Like I said, you’re not doing anything illegal and everyone in this situation is a consenting adult, but if the tables were turned you’d probably be doing everything in your power to break up your daughter and your friend.

In the end, here’s my advice: don’t tell your daughter. Break it off with Abby and make sure she knows exactly why you’re breaking it off, then swear her to secrecy; have her take this shit to her grave. In fact if you went so far as to murder Abby and bury her corpse along some long stretch of highway that’s still a better idea than what you’re doing now. Your daughter should NEVER find out what’s been going on, but if you don’t think Abby can keep her mouth shut for the rest of her life then go ahead and tell her. Tell your daughter you’ve been banging her bestie for restie behind her back for the past few months, beg for forgiveness while she’s in the ER with the heart attack you just gave her, and then hope to god she doesn’t stop speaking to you for the rest of her life.

And in case you’re thinking of ignoring everything I’ve said and continuing to date Abby on the down low, think of it like this: what are the chances anything actually comes out of your relationship with this girl? She is 17 years younger than you are. You’re not getting married. She’s still in school. She’s not even legally allowed to drink and the ushers checking IDs at R-rated movies probably thinks you’re her dad, which is a fair assumption considering SHE AND YOUR DAUGHTER ARE THE SAME AGE.

I know that was probably a bummer to read and you feel like any hopes at happiness you’ve let bubble up into your life have been popped. Being a buzzkill sucks sometimes and I have family members who are single and pushing 40, so I kind of have an idea where you’re coming from. Instead of moping around about how you and Abby broke up (WHICH YOU BETTER BE FUCKIN’ DOING SOON), think about the positives:

-You must be pretty attractive to have pulled Abby in the first place

-Abby chose to date you instead of the thousands of college boys ripe for her picking

-Your game is good enough that you were able to keep her interested in you for more than 20 minutes

That right there is pretty impressive. I’ve met my dad’s friends and they’re all boring as fuck and don’t know how to talk to me, so take solace in knowing you’re probably genuinely cool and not some creepy perv who bangs barely-legal girls. You already knew that, but I just wanted to make sure you didn’t think I thought you were a creepy perv who bangs barely-legal girls; really, you’re just old and lonely. We’ve either all been or will be there, so next time you go looking for a date try to avoid anyone under the age of 25 who happens to be close friends with your daughter. There are plenty of fish in the sea my friend, just because one bites on your line doesn’t mean there’s a better one out there waiting to be wooed by a cheap piece of sparkly plastic shit from Wal-Mart.

Do you have a question for our resident pink-haired…whatever she is? Email!


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