Dappered

Affordable Men's Style

  • Don’t Miss Anything
  • Start Here
  • Essentials Shop
  • Latest Deals
  • Style Scenarios
  • Reviews

My girlfriend’s cleaning out my wallet…help!

July 20, 2016 By Beth | Heads up: Buying via our links may result in us getting a commission. Also, we take your privacy rights seriously. Head here to learn more.

Hi Beth,

I have been seeing an incredible, strong, independent woman for several months. We haven’t put a label on our relationship but things have gotten somewhat serious pretty quickly. There’s just one issue…

On our first date I noticed she didn’t even make the traditional fake attempt to grab the bill. No big deal, right? Except that she hasn’t made an effort to pay on a single date since then. We hang out 2 – 3 times a week and I would estimate that I’ve paid for at least 90% of our expenses. Recently, at dinner, she mentioned she didn’t want a second drink because I always pay. I claimed it didn’t matter (it does) but then brought it up in conversation a few days later. HUGE MISTAKE. I won’t bore you with all the details of our argument but it was a big one. Eventually I backed down and we’ve made up.

I’m more than a bit concerned by the precedent that’s being set going forward. Now, I’ve been in the working world for a few years and she just recently finished her undergraduate degree. I have a great job that pays quite well for my age and location; however she will be starting a similar job shortly with almost the same salary. Additionally, she worked through college and is good with money so she definitely isn’t broke.

Who should be paying at this stage? Is this a deal-breaker at this point in the relationship? Is it a deal-breaker if it doesn’t change in a few months? I’ve dropped it for now but how do I bring it up again and when?

Thanks,

Newly Broke (but smitten) Brad

 

Maybe Brad’s girlfriend has alligator arms?

Hi Brad,

I think a lot of people can empathize with what you’re experiencing. At the beginning of a relationship, all sins are forgiven. Someone has bad table manners, or throws wet towels on the floor, or drives like a maniac–it’s easy to avoid these issues because the endorphins of new love are clouding your brain…and it’s also daunting approaching conflict with a new person.

Your financial positions make this sort of negotiation awkward, as you’ve sussed out. She’s not going to be able to afford the types of restaurants and outings that you can afford. And yet, she’s about to join the ranks of the gainfully employed. I don’t think it’s terrible that you’ve been paying all this time. I mean, even a college student with a job is likely broke. If you’d written in sooner, I would have encouraged you to seek out free activities–concerts in the park, picnics, bike rides–or ones that are relatively cheap–drive-in movies, coffee and dessert, bowling–so that you didn’t feel so taken advantage of, and so that she might have the opportunity to offer to pay. As it’s been, dinner and drinks for every date is pretty expensive, right?

ExpensiveJerryBrad feels your pain, Jerry. (image credit).

In an ideal world, she would offer to pay, like, even 1 in 5 dates, or she’d take the initiative and plan some of these no-cost dates. Why hasn’t she? I don’t know. But it sucks. It’s certainly an outdated attitude, and one that I don’t think most modern women share.

So how do you address this with her? The first mistake you made was lying at dinner about not caring that you always pay for everything. FYI, that was your lady trying to broach the topic, because she has picked up on your discomfort with the arrangement. I don’t know how you brought it back up several days later, but I’m guessing it wasn’t super smooth (second mistake) if it led to a huge fight. And your third mistake was backing down during the argument in order to placate her. Eesh.

My girlfriend's cleaning out my wallet...help! | Ask A Woman on Dappered.comJust gettin’ ready for date night…hmm…maybe I should take out another hundo. (image credit)

The good news is, the damage is reversible. Broach the topic with her (waiting a month or two until she’s entered the world of adult paychecks is smart). Not while at dinner, the movies, or anywhere else that you’ll be expected to pick up the check. Not after either of you has had anything to drink. A Saturday morning at home is ideal. A Sunday afternoon walk would work, too. Be honest. It bothers you, you should have brought it up earlier, you’re sorry that the one time you did try to talk about it, you blew it, but you want to be open with her, and it makes you feel sort of rotten to always spring for the check. Be prepared for some embarrassment and defensiveness on her part. Money talk does not bring out the best in anyone. If the conversation goes poorly, that’s ok, let it sit with her. She may come around. If she doesn’t…then you have to decide, based on your own values, if it’s worth staying with her.

-Beth

 

You're hovering a bit there bucko.

About the Author: If you’ve got a question that needs the female treatment, chances are you’re not the only one who wants to ask it. Beth is our source for the answers. From opinions on men’s style to decoding the sometimes mysterious ways of women, she’ll take on a different question every week. She also might provide an answer without waiting to be asked. That happens from time to time too. Click here to get to know Beth, then get in touch with her by sending your question to: askawoman@dappered.com .

Filed Under: Women Tagged With: Ask A Woman, dating, relationships

Continue the Conversation …

Want to share your thoughts on this article? Send us a tweet, join the discussion on Facebook, or hit us up on Instagram!

Don’t Miss Anything

Subscribe via email to get articles in your inbox or add Dappered on Flipboard. You can also follow us on Twitter, Facebook, and Instagram. Or subscribe to push notifications to get alerts immediately.

New Here?

Well, welcome to Dappered. Here are what we consider the most useful posts on the site if you're looking to put a little more effort into your appearance. Just want to see our favorite menswear products? Shop our essentials here.

Double Time: The Affordable Two Watch Collection – Under $300

Double Time: The Affordable Two Watch Collection – Under $300

A series for those who want all their style bases covered by two watches.

Steal Alert: Old Navy $16.99 Tech Shorts, $9.99 Tech Polos one-day-sale

Steal Alert: Old Navy $16.99 Tech Shorts, $9.99 Tech Polos one-day-sale

It’s a one day 50% off active wear sale, and their best bang-for-the-buck tech shorts & polos are getting the half off.

Monday Men’s Sales Tripod – The $49 Garment Duffle, $15 off $100 at Madewell, & More

Monday Men’s Sales Tripod – The $49 Garment Duffle, $15 off $100 at Madewell, & More

Also, putting together outfits to take advantage of BR Factory’s 50% off + an additional 30% off $100.

Follow Dappered on Instagram »

Men’s Fashion or Affordable Style?

Men's Fashion or Affordable Style?

Fashion is temporary and expensive. Style is timeless and affordable. Dappered® helps you work the retail system so that you can be comfortable, look sharp, and save money.

Want to share a great product? Email Us.
For a fit perspective, see Joe's measurements.
Make sure to read our affiliate disclosure.

CONNECT WITH DAPPERED

Thanks! Check your inbox or spam folder to confirm your subscription.

  • Facebook
  • Instagram
  • Pinterest
  • RSS
  • Twitter

Most Popular on Dappered

  • Kornacki Khakis for $33, Bonobos Throwback Trunks are back, & More – The Thurs. Men’s Sales Handful
  • In Review (and win it): The Q Timex GMT
  • Monday Men’s Sales Tripod – The $49 Garment Duffle, $15 off $100 at Madewell, & More
  • Steal Alert: J. Crew 25% off STACKING select full price, Extra 50% off Sale Items
  • Style Scenario: The “Classy”(?) Hungover Brunch
  • Steal Alert: Old Navy $16.99 Tech Shorts, $9.99 Tech Polos one-day-sale

Popular Topics

  • Best dress shirts to own
  • Best looking watches under $100
  • Best men’s dress shoes under $200
  • Nike Killshot sneaker alternatives
  • How to wear a suit without a tie
  • Suitsupply store review
  • Suitsupply Blue Line review
  • J. Crew Factory Thompson suit review
  • How much does it cost to tailor a suit?
  • Dopp kit essentials
  • Brown shoes with gray pants
  • Men’s style buying guide

Copyright © 2022 Dappered.com | Dappered, LLC | Dappered® is a registered trademark of Dappered, LLC

Hat tip: Magazine Pro Theme On Genesis Framework

Dappered does not collect or sell its users personal information | Disclosures: Privacy and Affiliates, Gilt.com, FTC

WPE

We work with partners that use cookies to understand how visitors use our site. Find out more.