It's 5:30 PM EST. The latest I've ever started one of these. I got engaged this weekend. Which means this is the part of Dumping Them Out where I pat myself on the back by saying, "You know I could have just blown this off, but since I'm a hero, I found time in my incredible important weekend to spend an hour writing a blog and posting some Boob GIF's." So congratulations to me. Both for getting engaged and for writing a single blog on a Sunday. Not many people in the world could work as hard as I do. That's the Barstool difference.
Since I got engaged this weekend, I'm now able to talk down to couples who have not yet gotten to that point. I can say things like, "You'll understand once you're engaged." So this blog is going to be me telling you the best and worst ways to get engaged.
Best: Central Park
Here's what you do. You tell her you want to take the dogs to the city on Saturday morning. She might say, "Well I have yoga every Saturday at 12", but just power through that. Don't give her the option. Also make sure her friends fly in the night before and have them waiting somewhere in the park to surprise her afterwards. Also, make sure you have a photographer. Tell the photographer to meet you at the Artist's Gate entrance to Central Park, then follow you around the little pond that's right there until you find a place with little enough traffic to do the whole down on one knee thing. But make sure you actually ask "Will you marry me?". I forgot that part. Did the whole speech and everything and she was like, "You didn't ask…." so that wasn't great, but overall that's an easy and good enough way to do it that won't get you yelled at.
Now you might be thinking to yoursself. "Isn't Central Park a little cliche?" The answer is no. It's not. It's creative and cool and everyone loves it a lot. I would be proud of anyone who came up with such an incredibly creative idea. Hypothetically speaking of course.
Worst: Sporting Event
Unless you're in the market of getting roasted, or you have one of those girlfriends who fucking love like, that Sacramento Kings or something, then don't do this. But honestly, if you're dating a girl who loves the Sacramento Kings, then what the hell are you doing? Unless she's really hot. But if she's really hot and loves the Kings almost makes it worse for some reason. If there's a super hot girl who loves the Kings, then there's something horribly wrong with her. You're going to wake up one morning with a knife to you throat the morning after the Kings are eliminated from the NBA Mid-Season Tournament.
Best: On a Remote Island Named after a Saint (Not Little St. James)
If you can acquire a boat, even better. I feel like any proposal on the water is a good proposal. You can't do it on a pond or a shitty lake, but if you can get to one of those islands named after a saint (St. Thomas, St. Ives, St. Croix), then that's an easy winner.
I actually don't know what Little St. James is like nowadays. Epstein is
in jail dead so I guess it's probably a fine island. A lot of weird shit happened there though so it's probably best to not use that one.
Worst: Anything Involving a Flash Mob
If at any point you find yourself thinking a giant group of strangers who you acquired via a Craigslist ad breaking out into a choreographed dance in a public area would be a good precursor to you dropping down on one knee and asking someone to spend the rest of their life with you, you should take a long look in the mirror and
kill yourself reconsider your actions.
Best: While You're Skydiving
I don't know if this has ever been done, or how you would pull it off, but if you could pop the question and pull out a ring while you're plummeting 120 mph towards earth. That's really cool. Again, idk if it's possible to skydive that close to someone. There's a good chance that right after you pop the question, when you pull your parachutes, the parachutes get tangled and you plummet to you death. But if you can make it happen it would be sick. But also… that would kinda be the best way to die right? During the best moment of the happiest day of your life. Marriages only do downhill after the proposal, so you might as well go out on top.
Worst: While in Bed
This might be unfair to say. Proposing in bed could be cool in some circumstances (I guess). Like if your bed is on a island named after a saint. But that's just lazy. I know there are some romantic things about it, but you gotta put more effort into the planning than that.
Best: During Sex While You're Busting
Ok ok ok so come to think of itk, maybe the proposal can be in bed if it's mid-bust. Has this ever been done? A mid-bust proposal? Holy shit that would rule. Especially if you had a photographer to document the whole thing. That would be an awesome porno too. You'd probably be making a weird face in all the pics but that's ok. A mid-bust proposal is really dope.
Worst: While You're Wearing Some Sort of Costume
If you ever find yourself in costume you should not propose in that moment. I don't care how much you and your loved one are into furry conventions. Or how much you love Halloween. Just be dressed like a normal adult.