This Girl Went On A Bad First Date With A Finance Guy Who Gave Her Tips On Her 401k

by Candice Jalili

This week we have Natalie* who went on what is quite possibly the worst date of all time with a financial planner she matched with on Bumble:


I met this guy on Bumble. He seemed a little odd, but all of the best people are a little odd, so I decided to give it a shot. We had been texting a bit, and he seemed funny and nice so out of my better judgement, I said yes [to a date].

Monday, 12:50 pm: Date is being set up.

He asks me what direction I'm heading to after work so he can look up a spot. He suggests the busiest sports bar in our city, and on the day of the NCAA playoffs. I kindly suggest another spot, and he suggests dinner.

5:46 pm: I arrive to this (completely empty) hole-in-the-wall Thai place in Chinatown.

It's one of those places people only go for lunch.  My date is nowhere to be seen.

5:55 pm: He arrives.

He rolls in and asks why I didn't tell him I was there (I did).

6 pm: We order.

Just water for him, so water for me too, I guess. Bad move.

6:10 pm: His appetizer arrives.

He doesn't share. And he starts showing me his Snapchat, which features him making Top Ramen and saying something racist about taking public transportation.
He starts showing me his Snapchat, which features him making Top Ramen.
I make a joke about being a professional Snapchatter. He doesn't laugh.

6:15 pm: The food arrives.

We start chatting about our jobs. He works in personal finance. It starts going downhill fast.
He asks me, "Don't you get a pension at your company?" And I was, like, "yeah," and he starts asking me all of these questions about my 401k and whether or not I have Roth or IRA.
He starts asking me all of these questions about my 401k and whether or not I have Roth or IRA.
He specifically asks me how much money I'm contributing from each paycheck. I laugh and realize he isn't joking, so I awkwardly answer.

6:20 pm: Turns out, he only knows one restaurant.

I ask him why he suggested this restaurant, and he told me, "It's the only place I know. I don't get out much."
I awkwardly laugh until I realize he's serious.

6:25 pm: He asks me what I do in my spare time.

I offer up some interesting things about me and tell him I'm a volunteer at a dog shelter. He tells me he's a cat person and hates dogs. Oh no.

6:30 pm: The check comes finally.

I reach for my wallet, anticipating he will tell me to put it away. He looks up and says, "So should we split this?"

6:35 pm: After awkward small talk, the check comes back.

He asks me how to spell my last name so he can write this off on his taxes as a business meeting. I try to laugh this off again, when I realize, once again, he's serious.

6:38 pm: He's serious as ever.

Dude has still not cracked a smile.

6:40 pm: I'm trying to leave at this point.

I've made up a Barry's Bootcamp class at 8PM to get out of chatting with him more. As I'm leaving, he asks how much money I save monthly. When I tell him, he asks if I'm "freeloading" and not paying rent myself.
As I'm leaving, he asks how much money I save monthly.
He then asks if I would be interested in having him run my current finances through his system. I turn and leave.

7:24 pm: I get an immediate follow-up text.

He texts me his email address and tells me to send him my benefit information and add him on Snapchat.
I do neither.

BONUS: He followed up about the benefits a week later.

Read it for yourself and cringe away.


I would give $8 million to someone who's managed to get an even worst date story. (OK, fine. I don't have a $8 million to give you, but I would laugh really hard, and that should be enough, right?)

It just has so many layers of awfulness, ya know?

First off, picking a weird empty restaurant on a first date probably isn't a good idea. Then, admitting that the aforementioned empty, weird restaurant is the only restaurant you know is probably an even worse idea.

And let's not forget how he proceeded to make racist jokes to this stranger. That's the only way I can think of to make this date worse.

OH WAIT, asking the stranger how much money she makes, saves and invests is probably worse.

Then of course, there's the whole splitting the check and admitting you're going to declare your half as part of your tax write-off factor.


Let's all keep our girl Natalie in our thoughts and prayers.

I think we can all agree she's WAY better off single than she is dating guys like this dingus.

*Names have been changed.