A Special Ep. of TILU: Dating 101// Who’s Paying?

11 December 2019


Times have changed since 10 years ago. With apps like Tinder, Grindr, and Bumble it’s like you never actually have to settle on one person. Don’t get confused: I didn’t say settle (you NEVER settle) but settling on one person… isn’t that what the goal of dating is unless you enjoy dating multiple people at once? Side note, I watched Polyamory: Married and Dating on Hulu because I was so bored and it was a great show. Not my style, but great show. 

Here’s the thing. 20 years ago, you had to pick up a phone or write a letter to ask someone out. From the beginning of time, way before #MeToo, men were expected to make the first move. I always thought that was weird. Like, if you’re hot and I think you’re hot, I want to get to know you. You might be hot and an asshole but until I ask you out I’m not going to know that, will I?

I dated someone for three years and guess how we started going out? I wrote down my name and number on my business card at a grocery store in Connecticut when I was living in Boston (home for the weekend) and I went up to him. It was scary and I was 18! But I don’t care about rejection and never did. So I asked him out and we dated for a long time. To this day he says he would’ve never asked me out because I looked “too intimidating”. I could’ve waited for him to ask me out that day but I knew he wasn’t going to because nowadays, men don’t do that as often. It’s easier to swipe right and left then it is to also go up to someone you think is attractive.

IF you fail to play the game, you’re going to lose. This year in particular I’ve been asked out a lot, which is different for me because I always seem to be the one asking out, and all three times I started seeing men (one I met at my WeWork office, one at a wedding, one at a restaurant in Connecticut, one through a friend)…

I got ghosted on the third date. Two/five I was asked to split on the 3rd date with older men- way older than me who asked me out. I live in LA, it’s not like these bills come out to $16 and some pennies.

The weird part: three of them were over 35, one was 26, and I got asked to split the bill on the third date by the oldest two men. I can pay my bill and yours plus 30 of our friends: this isn’t about the money. This is about your morals and mine.

Out of curiosity I asked every single one of my girlfriends this week (between 25- 40) and I called my mom…they all agreed that men over 35 shouldn’t ghost and that they should definitely pick up the tab post third date. I’m not disclosing whether or not I slept with someone/none of them/ any of them because I’m not letting that alter anyone’s opinion on this topic. BUT why aren’t the younger, less established ones asking to split the bill but the rest are? AND, why did so many vote on my Instagram poll saying they WISH the woman would offer? What if she paid for the Ubers or one round of drinks? Do you want us to stand on the bar and scream “HEY, MY TREAT!”

Dating for me is very difficult. I don’t usually disclose my age because it scares older men off until they Google me- I starting dating older guys more recently (I’m too busy and not interested in frat parties/ partying to care about your beer and boredom)  and I’m not on dating apps anymore (besides Raya) and that’s what spun me into wanting to have this conversation.

I get it, I’m successful, but so are you if you’re over 27. According to the messages I got on Instagram, you’re all offering to split the bill on the first date (girls and guys). In my opinion, if you’ve met on a dating app, I’d offer to split the bill. I would. Serial dating is a thing in 2020 and no dude is interested in paying $100 a night every night of the week if they’re going out every night. We’d like to think we’re that special fun diamond who will make a guy settle down just by looking at us but unfortunately unless you really get to know someone, they’re probably comparing you to the 20 other girls they’ve gone out with that week (or night)!

Only a few of many messages we got on this topic from you…


Here’s my opinion: I think the guy should pick up the tab from the 1-3 date. If he’s older and getting to hang out with you, then why not the 4th date? But, if I’m going out with someone in a random city and I downloaded Bumble just to have fun, I’m offering to split the bill. Most of my friends agree with this, but I think it also comes down to your personal morals. I got messages from people asking how to “bring down” their expectations so they’re not single- f*** that. Don’t bring down your expectations, let them meet you at yours. No more half put your hand in the bag: you either offer or you go into a date with the expectation it’s important to you that he/she pay. You can easily use this thing called communication and communicate at the beginning of the date with how it makes you feel when people ask you to split on the first date. Then it’s up to them to step up to the plate, or you split and leave! No guy or girl is worth sacrificing your expectations for.


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