Love + Money: Dating 101 - What's "Normal" Anyway!?

Love + Money: Dating 101 - What's "Normal" Anyway!?


Hi Friends! We are SO excited to bring you today’s blog post - the latest installment in our Love + Money Series! We’re getting into some of the money “deal breakers” in a relationship, some of your biggest financial pet peeves + so much more! Our past Love + Money posts, including how to build a budget with your S.O. + how to discuss your financial background, can be found HERE.

It’s been a few years since we were in the dating world (like 6+ years…), but after several recent girls’ nights hearing from our friends, we realized that there’s some variability in what’s expected now in dating + that even in serious relationships, there can still be frustration around finances. We decided to see if we could find a consensus from our readers on what’s the “norm” for dating + money in 2019, as well as share our opinions too!

A few months ago, we took to Instagram to get your opinions + stories on Venmo etiquette, splitting bills with friends, etc. + surprisingly to us, it was one of our most popular pieces to date + can be found HERE. Because of how much you all loved the post + how helpful we found your participation, we decided to crowd source again for this piece!!

If you want to get in on future polls + help contribute ideas to the topics we address, be sure you’re following us HERE on Instagram - @hellohenrys! We post so many travel + finance tips each month that don’t exactly warrant a whole blog post on our site, but are super helpful nonetheless! So, if you’re at all interested in taking a trip on points, where to allocate extra debt payments, etc., be sure to follow along!

So without further ado, let’s get into it! Remember - as with anything in life, especially with money, there is no right answer, we’re simply sharing our take and opinion! :)

Would you date someone who makes significantly less than you?

67% of you said YES.

K: Yes. I feel secure enough in my finances + budget that I know that I can accomplish the financial goals that I have with solely my income, even as a teacher. I would have no problem dating someone who makes significantly less than me as long as we were on the same page with budgeting + financial goals.

L: Yes. To me, the amount of money a person makes isn’t a guaranteed indicator of the kind of life, you could expect to lead with them. Over 25% of America’s upper class lives paycheck to paycheck, so, from that alone it’s clear that more money doesn’t always equal a more stable or comfortable life if the right foundation isn’t in place. To me, I care about being able to openly discuss money + being equally motivated about financial goal setting, not how much is in someone’s paycheck. Also, being around someone who is passionate about + fulfilled by their job is a huge plus in my book, regardless of if they take home $50K or $200K.

Do you expect to split the bill on the first date?

64% of you said NO.

K: Yes. This one actually surprised me, but I think that it has to do with the phrasing of the question. I think if I’m going to go out for a meal, for a drink, whatever it is, I should be going with the expectation + means to pay. If someone else offers to pay, great! But I’ve never had the expectation that someone else should be paying for me. So I would never be offended if on a first date I split the bill with my date. However, I do recognize that I’ve never been asked to pay on the first date + that there is 100% still societal expectations there that a guy will pay on the first date - which is where I think the phrasing of the question affects my answer.

L: No. I don’t expect that I would split a bill on the first date, but this is primarily because I never have actually been asked to or had my offer to split accepted. That being said, it would not be a deal breaker for me if a check had been split at the end of the date. If I enjoyed the person’s company, I would be open to a second date regardless of how the checks were split up. I totally get tradition though, so no judgement if splitting is a deal breaker for you!

Would you break up with someone if they had a different financial mindset than you?

68% of you said yes.

K: Yes. I think at the end of the day, there’s a reason so many divorces can be traced back to finances. It’s important to have similar financial mindsets + goals because it impacts SO much of your day to day life. It’s hard to not be on the same page because that will affect how often you’re going out to eat, where you’re living, what you’re doing in your free time, etc. I just don’t think it would be a viable relationship if I didn’t have the same financial mindset and goals as my partner.

L: Yes. However, I think this question is open to interpretation. “Mindset” could mean so many different things. I am actually not of the opinion that both partners have to be either “savers” or “spenders.” I think having different attitudes + behaviors toward money can actually provide a healthy balance for both people. However, how I took this question, was more around long-term views + decision making. For example, I know that, for me, a successful relationship with someone who thought credit card debt was no big deal, didn’t invest for retirement, have a savings account, etc. would be very challenging in the long run + I would probably break up with them.

When do you think you should talk about finances in a relationship?

50% of you said “Once You’ve Had the DTR Talk”

44% of you said “Only Once You’re Moving in Together”

K: I think to talk about finances when you’ve had the DTR talk + when you’re moving in together are two very different conversations, but both important ones to have in order to move the relationship forward. By the time you’re in a relationship, I think you should know that you have similar goals when it comes to money so that neither of you is wasting your time. However, I think once you’re moving in together or getting married, then it gets to more of the nitty-gritty numbers. If I’ve moved in with someone, I’ll want to know more information since I’m taking on a financial responsibility with them + their financial choices now impact me.

L: I think conversations about money are important to have frequently throughout every stage of a relationship + will be different at every stage. Prior to having the “DTR Talk,” I think you would likely be able to pick up, high level, on how a person spends money + what’s important to them. I would probably be willing to be “official” with someone prior to having this conversation, but would broach it as the relationship was becoming serious. At that time, I would want to know more specifics, such as whether or not they have student loan debt, a retirement account + what they earn. After moving in together, I would take this one step further + share exact credit scores, bank account balances, etc. Each conversation progresses with each stage of the relationship. I highly recommend a quarterly money date, even years into the relationship, to continue these conversations + stay on the same page.

What are your money pet peeves?

When a guy doesn’t pay more because girls spend more on prep.

K: I don’t really agree with this one. I think that all of the money I spend on “prep” (make-up, hair care, etc.) are all things that I would be spending money on regardless of if I was looking for a relationship. I like to do my make-up + spend money on that because I feel good when I do, so to me I don’t see that as a trade-off in the relationship then that the guy has to pay more on a date just to make up for the money I spent on my foundation or hair cut…

L: This one is a little tricky. If the partner who is spending more on “prep” out-earns their partner, doesn’t have any debt while their partner does, etc., then I don’t think it is fair to expect your partner to “chip in” solely because of your beauty expenses. In general, if one partner is significantly more financially comfortable + is suggesting activities that the other person otherwise could not afford, then I do think it would be nice for them to pay a little more or offer to pick up the entire check once in a while. However, this is an important topic to discuss. If you can’t afford to do the same trips, activities, etc. that your partner can, it’s good to get on the same page about expectations.

Wasting money/making poor financial decisions

K: I think this goes back to why it is so important to be open with money + be on the same page. I would be really annoyed if we’re always needing to stay in on a Saturday night if my partner wants to save money, but at the same time see them splurging on random items or finding the money to be able to go out with friends on Friday nights. However, that doesn’t necessarily mean that it’s a poor financial decision, it simply means that our financial mindset or goals don’t align + that maybe this isn’t a relationship I should be in. I’m sure plenty of people out there think that the money I spend on clothes or travel is a “waste,” but to me, that’s a priority that I have + am willing to spend on.

L: Speaking of pet peeves, the term “wasting money” actually really bothers me. Primarily, because it is so often used to mean “spending money in a way different from how I would.” Calling someone else’s Barry’s Bootcamp membership a waste of money just because you choose to run outside or not exercise at all isn’t fair if it’s something they value + can afford. There are so many examples of this - my friend’s UberEats order is a waste of money because I choose to meal prep at home, a car payment because I choose to take the bus, etc. etc. ETC!! If someone spends money on the things that they value, prioritize + can afford while checking off other financial milestones, that is their business. Different does NOT equal “waste.”

Rant over though hehe - I totally get what (I think) this person meant. It’s super frustrating to hear someone talk about how they want to build an emergency savings account, but then continue to dip into it to fund a shopping habit. Again, so many examples could be given, but the point is, if someone is making decisions that you know don’t align to their goals or are decisions that they openly regret, but continue to make, then yes, that absolutely would + does bother me.


Venmoing the same $20 back + forth forever, just trust it’ll even out

K: YES! I think when you’ve been in a relationship long enough, but don’t necessarily have joint accounts or anything, it can be so tiresome to Venmo the same amount back + forth. Some times I will pick up the dinner tab, + sometimes Elliot will pick it up. We’ve been together for over 7 years + frequently eat out, so I just know it would be the same money going back + forth. I’d rather call it a wash considering we spend so much money together. I actually don’t feel like Lauren does at all. I never view that as “owing” him money or him “owing” me money. With a friend, maybe it’s a little different because you aren’t spending as much money together, but in terms of a long-term relationship, I think I’d spend way too much time on Venmo sending $20 back + forth to cover that bottle of wine or that dinner. Obviously, for larger financial purchases, such as a flight, I’m 100% going to send a Venmo.

L: In general, this does not bother me. I know this comes up as a pet peeve in any level of relationship, whether it be casually dating, between friends, etc. I actually feel the opposite to some degree for multiple reasons:

1) In general, I just don’t like feeling like I owe somebody else money + would rather keep it even.

2) So many times people aren’t explicit that they are picking up the tab + then I live in a constant state of “purgatory” of wondering when they are going to send me a Venmo + then awkward if I have to send them one for something else. It’s like “UHHH…do I deduct the amount of my glass of wine they covered last week from this!?” This may just be my own dramatic, overthinking tendencies though.

3) If I go out with a friend + budget a set amount for the evening, which I often do, let’s say $25 + the bill comes to $50, I wouldn’t want to pick it up just to prevent sending a $25 Venmo. I budgeted for $25 + that’s how much I want to pay.

Basically, if I want to treat a friend, I want to treat them without the expectation of it ever evening out. I just want it to be a gift or a random act of kindness. If I have an expectation of it evening out, then yes, I will send the $20 Venmo!

If you ARE going to operate by this mentality, that’s totally fine + I’m probably the weird one, but I would suggest making sure your friend is on the same page + not just decide for them.

Mandating someone split the check or pick up the next tab

K: If you’re going to trust it’ll even out (like I said I do with Elliot above) then you also can’t be the one saying “Remember that time I bought you lunch 3 weeks ago? This one’s on you.” I think you also have to recognize that there’s a risk (if you can even really call it that) that when you buy someone something, it may not even out or be paid in return. Don’t make it awkward. If you don’t feel comfortable with the chance it’ll never even out or aren’t paying for something because you want to…then just don’t do it.

L: OMG just got so uncomfortable just reading this. I feel like there is a story behind this…if so, whoever submitted this, please DM us. We (aka mostly me) are admittedly very nosy. Similar to the pet peeve listed above, if you ARE going to operate under the “it will even out” mentality, you don’t get to decide when that happens. Whether with friends, family or an S.O., money should always be a discussion, not you deciding what the other person will/won’t do.

Stupid debt.

K: 100%. Student debt, sure. $10,000 in debt from having too much fun + no plan to pay it off quickly or have learned from it, no thanks. (Yes, this follower who DMed us actually did have an ex with all that exact amount of debt + absolutely nothing to show for it).

L: This is situational in my opinion + depends on the amount. Early on, I shared my story of racking up $4000 in credit card debt essentially from spending an entire summer at Safeco Field. And before you ask, no, I am not a baseball fanatic. I did, however, prioritize getting out of this debt quickly + have laser focus on getting back into an excellent credit score range. You can read more about this story + how I made that happen HERE. Stupid debt without an action plan to get out of it or some kind of awareness/learning would for sure be a pet peeve.

Flashiness of one’s income

K: I’ve never really thought about this one, but I can see it being a pet peeve. I’ve always had way more respect for people that come from a lot + are able to have nice things without overtly showing it off.

L: Yes! Flashiness of anything, not just income, always, in my mind, signals an insecurity about something else + is a big pet peeve. The stereotypical guy who talks about how many girls he dates, the co-worker who mentions multiple times a week she attended Harvard, etc. In my opinion, being humble, at the right times, is such an important trait that most people (myself included times ten) should always be working to cultivate + is one of the qualities that is common in almost all of my close friends + family.

Well - there you have it!! That was SO much fun + that’s not the glass of wine (jk-two) that we drank while writing this talking. We absolutely LOVE interacting with you all to learn more about your perspective on money + opening up the topic for conversation in general. If you like reading these opinion posts + seeing how many peers vote for the same/different things than you do, let us know + we’ll for sure keep doing them!! Thank you thank you thank you for reading + following us! We officially have QUADRUPLED our viewership from last year + only want to continue to grow. If you find any of our posts helpful, the highest compliment is to share with a friend, tag us when you visit a spot mentioned in one of our travel guides, even just a like on the ‘gram!

Talk soon!! xoxo


Breaking Down Our Budgets: How We Nail Retirement Savings, While Still Going To Soulcycle + Sushi

Breaking Down Our Budgets: How We Nail Retirement Savings, While Still Going To Soulcycle + Sushi