Keep The Receipts: A 29-Year-Old Woman Dating Post-Divorce

Illustration by Seeta Kanhai
In our series Keep The Receipts, we track the extravagant costs of everyday living, as well as the less-common expenses tied to other life moments.
Last month, we talked to a non-monogamous man in his early 30s who spent much more money on dating than he realized. Previously, we spoke to a woman who made a road trip out of her cross-country move.
This month, we talk to a 29-year-old woman who moved to Chicago on the spur of the moment after an unexpected divorce. As she revealed in her Money Diary, her cost of living changed dramatically after the separation — and so did her dating life.
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Ahead, she talks about the often fraught dynamics of learning to date again in a brand new city.
Want to Keep The Receipts? Tell us about about your month of moving, dating, weddings, and more at moneystories@refinery29.com.
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"There are 12,000 shades of relationships. What was once easy to figure out is now much harder."

Refinery29: In your Money Diary, you talked about dating being weird and interesting post-divorce. Tell me more about that.

"I was with my ex-husband for almost eight years. Tinder and Bumble and dick pics did not exist back then, and now they do. It was like being thrown into the ocean without a life vest. My ex-husband had a whole secret family and he divorced me out of the blue one day. I had no idea I was going to be dating again, and it was a very jarring change. The first [Bumble] match I made, the guy sent me a dick pic via Snapchat about 30 minutes into the conversation. I was like, I quit. I’m done. I’m not doing this anymore. It was startling."

How did he have your Snapchat?

"I had just gotten Snapchat after my divorce, so I was social media ignorant. He asked if I had it, and I was like, 'Yeah! Why?' He said, 'Oh, no reason…' and my phone number was linked so that happened. I deleted Snapchat for like six months. I was like, I don’t need this..."

What were your experiences dating before you got married?

"It was in the deep south of Georgia in Savannah. I married The Frat Boy and dating him was a very respectful thing. We moved in together right away and it was just a given that we were in a relationship. Now I feel like there are 12,000 shades of relationships; what was once easy to figure out is now much harder."

You also said that you asked your friends in their 20s what dating was like and what to expect. What did they say and did you trust their experiences?

"Weirdly, three of my closest girlfriends have also gotten divorced. One was my high-school best friend, and the others I met throughout my life. There’s a strange level of closeness you establish because you're like, 'Look! We’ve all been traumatized this way.' What is interesting is that everyone's experience kind of correlates to how much therapy they have done or how much closure they had.

"I did a lot of therapy the minute my [marriage] started to tank because I didn’t want it to scar my entire life. Obviously, it’s a big deal and it definitely had a huge impact on me, but I didn’t want to hold onto that for years and years. I started dating a lot faster than some of my girlfriends who had been divorced for six months. I figured out that the less therapy they had, the longer it took them to start dating again, and the worse experience their experience was."

How soon did you start dating after your divorce and did you feel judged for doing so?

"My wedding planner actually introduced me to a guy about 30 days after my divorce started. It was a very casual thing, but it was exactly what I needed. I don’t recommend it for everyone, but it was what worked for me. It was a very good distraction."
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"I paid my half more on dates where I knew they would expect something."

What was your financial situation after your divorce?

"My ex-husband made $100,000. I recently figured out we were only seeing about half of that because he was funneling the other half into a slush account for his other family, but it was really startling. I went from a household that made about $170,000 combined, to just me living in a completely different city making $35,000 as a base and having to work for commission again. I was in a three-story farmhouse in Georgia. Now, I live in a 700-square-foot, two-bedroom apartment in Chicago. It was a huge change."

So you took a pay cut when you moved?

"I did. I owned my own business in Georgia and it was built on my ex-husband’s last name. I pretty much completely closed down the business and went back to recruiting when I moved to Chicago."

What were your thoughts on dating, money, and relationships in the past, and have they changed at all since your divorce?

"There’s a very chivalrous style of dating in the South but I actually think I split more on dates there than I do in Chicago, which was super surprising. I’ve only gone on one date I can think of here where we actively split because neither of us felt it. But I went on a couple of dates in the South where I paid for my half, and I was happy to. This is going to sound really bad but it was more on the dates where I knew they would expect something that I said I'd pay my half. I wasn't going to be giving anything up for that."

Do you think men in Chicago are much more aggressive about picking up the check?

"I went on a string of seven or eight first dates in a row over this month, sprinkled in with guys that I normally see. From what I can tell here, if a guy feels like it went really well and he had a great time, he tends to steal the check. I’ve gone on a few on dates where I could tell they just thought they were just chivalrous, and those were the ones where I very aggressively pushed my card at them, but they just would not take it. I’ve only had one date where I knew it was going poorly but I don’t think he did, and I picked up the entire tab. It was a small tab but I still picked it up because I wanted nothing to do with him ever again.

"Two of the guys I see regularly here make 10 or 12 times what I make; they’re at the top of their fields, they’re VP level — and I recruited one of them, so I know what his salary is. When I’m out with him, he really enjoys spending money. When the other one comes into town, his favorite thing to do is take me out and try new places. Another guy that always treats, whom I’ve dated on and off since I moving here, in the food and beverage industry and gets a massive discount. For example, we went to an incredibly nice restaurant for my birthday and probably should have gotten about an $800 check. But because he works in this industry and is friends with everyone, we only paid for our drinks; he always picks it up because he’s so connected.

"That’s the only thing I’ve really seen. In the South, honestly, the guys I dated made less money or equal to me, so it was more likely that if they really wanted to pick up the check and I didn’t want them to, I felt like they expected something, not that it was something they wanted to do."
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What is your ideal kind of date?

"That’s a good question because it ran the gamut over this month. Honestly, the best first date that I’ve had here was with Dave*. We went bar hopping and had appetizers along the way at about five restaurants in the West Loop, and it was a blast. It got me just drunk enough that I was super comfortable, but it was fun because I was seeing new restaurants. I met his friends and we bumped into my roommate at one of the restaurants. It was really carefree and fun, but I was seeing new things."

What do you think about equating the cost of a date with the quality of a date?

"The first date I went on during this timeframe spent well above $300 on dinner and 30 bucks on a nightcap. I paid for my Ubers to and from the date, and it was good in the sense that our conversation wasn’t too forced, especially for a first date. I didn’t feel any pressure and I did not go home with him after. I saw him again at the very end of the month — he's Date #19 — but it wasn’t like we set out to go out again.

"He’s a VP; he lives in [a very nice neighborhood]; he makes a ton of money, and his favorite move — and I know this because we met through friends — is to buy bottles of wine to try at dinner. He has no concept of what an expensive bottle is, so he’ll pick something and we’ll try it. It’s not a representation of how well the date is going or what he expects afterward; he just likes to try new wine, and he likes to try it on dates. I’m sure some of that is a maneuver to look impressive, but the other part of it is he just likes wine."

How do you feel about that — someone trying to impress you by spending a lot of money?

"I don’t care where a date takes me or what we do, as evidenced by the fact that the dates went from really high-end to dive bar. It’s more that I like to ask them where they want to go and what they want to do, and they can set the bar. If I have to sit there and suggest five restaurants only for them to go, 'Oh, I don’t want to do dinner,' well, maybe they don’t like me as much as I like them; it sets a weird precedent. I’ve also discovered that if I say, 'I’d love to go out with you one night. What do you want to do?' I can gauge their level of interest.

"I knew the guy on Date #1 wanted to take me on a very nice date, and I could tell he was interested in the way he approached me. He said, 'I’ll be in town on this date and I want to take you to dinner. Can you block off a couple of hours to spend time with me?' It wasn’t like, I want to take you to dinner and spend money. It was, I actively want to spend several hours with you. Is that okay? — and I’ve had a couple of very good dates like that.

"The guy I went on Date #3 with said something very similar. We went to a wine bar and each had a glass of wine and then went to a quieter sports bar where we each had three drinks and split quesadillas. I offered to split everything but he declined, so I only spent $7.65 on an Uber to and from the date. To ask me out, he said, 'Hey, I want to take you out to drinks and dinner. Can you schedule me for a couple of hours on this day?' That showed me he had interest in actually hanging out, versus, I’m going to take her out for dinner and maybe I’ll take her home. When it’s very loose or open-ended, I don’t know if they interested or if they’re just filling time."

Another Keep the Receipts interviewee had a similar feeling about guys showing initiative in choosing a date. Why is that so meaningful, especially since it sounds like you’re willing to make an effort?

"I don’t really know why per se. It’s just that I said yes to the date and, even though this sounds really terrible, in today’s society, saying yes to a date can get you killed. So many guys are like, 'Hey, wanna Netflix-and-chill?' on a first date, and I’m like, no. I want to meet you in person, in a bar, so I know you’re not a serial killer. The amount of effort they put into it, for me, shows me that they’re interested. I didn’t really notice until I looked back over these dates but I realized that the dates that went poorly were the first dates where there was little-to-no planning; the ones where there was a lot of planning, even if we just went to a dive bar, went a lot better."

Tell me about Date #2, which was also an expensive one.

"It was to a work holiday party with Eric that coincided with Date #1; they were right after each other, but I don’t normally double up!

"When my marriage fell apart, my entire life imploded and all of a sudden, I was in a big city. It’s a shock to your entire life. Eric is someone I recruited; he moved to Chicago to get engaged but he caught his fiancé having an affair. He lost all of his friends here because they were all hers, but he’d already left home and was also starting over in a new city. He’s struggling with it — probably more than I did — and we’ve been seeing each other since October. We are very clear on the fact that we’re good friends — we talk all day, every day — but he’s not ready for a relationship and I do not want to be his rebound. We usually go on really casual dates but when it came time for his holiday party, he knew he'd be surrounded by friends of his ex-fiancé's friends and he was a little nervous. He went to the actual dinner by himself and after, a group of people went out on double-dates at a bar.

"He knew I was coming from one and said, 'If it doesn’t go well or you have the time, I’d like you to join me and be my date for this,' and I said sure. I had no intention of hooking up with the first guy so I met him at the bar (my only expenses were my Ubers) and they all took turns paying for bottle service; that’s why it’s so freaking expensive. There were like four rounds and the total tab for the table was probably closer to $2,000 or $3,000; they each picked up their round of bottle service.

"It was a really interesting date for me. We were interacting with his coworkers, meaning there was pressure for me to behave, for lack of a better word, and it wasn't with a group of people I socialize with a lot. I have no interest in being a socialite, and going out every weekend, and dropping $1,000. More power to them — but it gave me some anxiety. I was like, Am I dressed nice enough? Is my hair okay? What am I doing with my life? My defense mechanism is just laying on my Southern accent. I wish I could say I manned up and was fine, but I just deepened my accent because I know people will get distracted by that instead of the other faux pas I’m making."

Have any of the guys ever made you feel self-conscious about that, especially since some of them make so much more money than you do?

"No. I knew that Date #1's favorite thing to do is go to fancy restaurants, so I came dressed up. By the time I made it to Eric's, my outfit transitioned nicely. But no one’s ever made me feel self-conscious about what I’m wearing. I’m really simple when it comes to dressing. I’m not going to go out and do anything crazy or wear a body-con dress or something. I tend to go with something I’m comfortable in and I know I'll look nice in — and I will 100% recycle that outfit through first dates until it sticks. I have no problem with that."
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In the second week, you had dinner in for Date #6. Whose idea was that and were the ingredients already there?

"That was Eric. We had talked about going out but I think it snowed a lot that weekend, so I knew that nobody wanted to go out or do anything and we stayed in at his place. I think I cooked for him one other time and I already had all my ingredients. He gets meal deliveries about once a week, so neither of us had to shop for anything."

Date #9 was also a no-spend date. Tell me about that.

"I adore him. We dated in college and constantly joke that we are the ones who should have ended up together but didn’t. We dated right before I started dating my ex-husband and it never materialized into anything, but when I started dating my ex-husband, he was really respectful and we’ve stayed friends.

"About two months after my divorce, he called me out of the blue saying he was in town and wanted to see me. I said I wasn't in a very good place, but he said, 'Hey, I booked a room at the W. Let’s get you a spa weekend and go out to eat, and it’ll be great like old times. I was sold.

"I was in town finishing up work for my old business, so we ate breakfast at his restaurant beforehand. I had to go work right after breakfast but he was like, 'Let’s go make out in the parking lot,' and I said, 'Absolutely.' He’s very sweet."

What was it like meeting for a date at a restaurant he owns? It seems like the dynamic for who pays would be much more relaxed.

"Yeah. I still took out my debit card fully intent on paying because I know it’s his business. But even though it was just breakfast, it made him happy to see me eating his food and get an opinion on what I thought."
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In Week Three, the first person you went out with was a Bumble date and you split the bill. Did you discuss that, and if so, how often does money come up?

"I’ve never had it come up. Because I’m a recruiter, I kind of have an idea of what everyone makes simply because that’s what my industry is; it’s a strange bit of insight. I kind of know when the playing field is level or when it’s exceedingly tipped in one direction.

"I played golf in college and this guy was more fascinated with my golf swing than he was in me as a human. He wanted to be clear that he was interested in getting drinks to get to know me, but that he didn’t have expectations for it to turn into another date or a relationship. He wanted to be really clear and I was fine with that. I’d never been to that restaurant, I don’t normally go out in that part of town, and I said I'd love to try it out.

"We did split it evenly; he had more drinks than me and he was a recruiter as well, but a corporate recruiter. Agency recruiters make a lot more than corporate recruiters, so I knew we were probably on an even playing field. Since he was really nervous about it being too serious, I was like, yup, split it, it’s not a big deal."

Why was he worried about you thinking it would be very serious? Did you state that in your dating profile?

"No, my Bumble profile literally says, 'Just ask me on a date.' That week, a friend gave me crap about only dating older guys, so I lowered the age down to 29. He was younger, and I’ve discovered that people in Chicago get married a lot later than people in Atlanta. I think he had just come out of something, he wasn’t into anything serious, and he wanted to see if there would be any chemistry; he did not want a relationship, but he does want to play golf.

Do you prefer older men because you think they’re more stable?

"I do prefer older. My range was 29 to 42 [after my friend's comment] and now it’s at 32 to 42 because all the guys who were younger that I went on dates with that week just come across young. That’s fine — but I’m 29 and divorced, and normally, younger guys aren’t okay with it. One guy even told me he doesn’t date divorcees because they 'obviously didn’t take their vows seriously.' He went back on it the minute he knew I was divorced, because he wanted to get laid. I would have respected him more if he had stuck to his guns but he’s Southern, and there’s a big stigma about dating divorced women in the South.

"All of my girlfriends that were divorced in the South struggled with dating. Mine’s a little bit better because I can say my ex-husband had a whole family; it’s a Lifetime movie. But some people say, 'Yeah, you know, it didn’t work out. I got married young,' and there's judgment.

"I have to gauge the conversation and figure out where they stand on it. I'll ask a question: What are your dating hard nos? Sometimes, they’ll say I should go first, and I’ll say, 'People who are rude to waitstaff is my biggest no-no.' I’m not okay with that. My other one is situational. I view children as something as I’m okay with or not okay depending on the relationship they have with their dad. If it’s tumultuous, there’s a lot going on and I don’t want to be a detriment to their relationship with their parent. You have to be really aware that you’re entering that child’s life and you’re impacting it, so you have to consciously date that person. Their child is involved and it's not fair to the child if it ends poorly and negatively affects them — or if I take it too casually and I’m just screwing their parent, that’s not fair, either.

"So, I set it up with that and wait to see what they say back. A lot of the times they go, 'Oh, I don’t really know if I want to date someone who’s divorced.' And I’ll say, 'Okay. That’s cool.' Some I tell that I am, and some I don’t. If they think it’s going really well and it’s not, I'll drop the bomb in hopes that they’ll back away from me."

When your date has more drinks than you — four drinks to your two, and on a few dates the drinks difference was drastic, such as 7 to 2 — does that impact your thoughts about who should be paying?

"Sometimes. Generally, I’ve discovered that the more they drink, the better they think it’s going, and then they’re all into getting the tab.

"Don’t get me wrong: I know people are super nit-picky about this. But look, if a guy is really leaning in to getting the tab and he’s had seven drinks and I’ve had one, I’m not really going to fight him. I’m just going to chalk it up to the fact that I’m a lightweight and he got probably a little too drunk on the date."

Is that a turnoff for you?

"It is. The guy from Date #18 was divorced as well, and it went really, really well in the beginning — then he hit drink seven or eight. I actually lost count of how much he drank.

"He got a little loud and a little clumsy, which is fine. I’m loud and clumsy when I’m drunk so I cut him slack on that. But we went to a diner after and he was rude to my waitress, yelling at her to get him his 'fucking card.' I was embarrassed because it was the corner diner that I go to once a week; the date just spiraled from there. I think he thought he was ready to date post-divorce but he isn't, and I’m not going to date someone who is mean to people when they’re drunk."

On Date #11, you paid the full tab. What happened there?

"He mansplained the fuck out of everything to me. I was doing the keto diet with my sister and he was telling me about this diet he was on. Instead of asking me if I was familiar with it, he just straight up explained it for 30 minutes. I fell asleep at one point; the bartender was dying.

"He showed up 15 to 20 minutes late to a bar that is literally on the same block as his apartment, whereas I had to take a $15 Uber across the city because I don’t live anywhere near there. When he arrived, he was pounding an Old Fashioned because he was nervous. I could tell when it hit because he started to lean in and was all in my face.

"The best part of that date was that there was a really hot guy sitting behind him. My date caught me looking over his shoulder at that guy one time because I was zoning out; the other guy happened to be taking a Snapchat of his drink — or maybe of my bad date — but my date thought he was taking a selfie and went, 'No one wants to see his ugly mug in a selfie.' And I went, 'I would. I would like to see it.' He really started drinking at that point.

"To make matters worse, when it came time to get the check, he leaned in and said, 'If you get it this time, I'll give you something better next time.' No second date."
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You also went on a few double-dates. What's the dynamic, in terms of paying, on those?

"Those are interesting — Date #19 was a double date, for example. I went with my roommate and her boyfriend, and the guy from Date #1. We drank cheap beer and it was a fun, laid-back time. We're very comfortable casually seeing each other with no pressure. I’ve discovered that if you’re out with a more established couple, my date will generally do whatever the couple that has been going out longer does. It’s like mirroring couple behavior off of theirs."

There are some dates where you commuted to a date, but didn't pay for it. Has that happened on a lot dates you’ve been on, that a date will pay for your Uber?

"Only with Eric really. Eric and a couple others. I know him better and again, he makes well into seven-figures so for him, it’s not a big deal. Even when I’m out but not with him, he asks if I made it home safe and if I need an Uber. I think because he lost all of his friends when his relationship fell apart and I was one of his very first friends here in Chicago, he’s protective of me. He knows my whole story, everything my ex-husband did, and he’s seen me when Dave disappointed me at some point, so I think he just wants to make sure I get home safe."

Dave is someone who also seems to pay for everything when you go out. What is the dynamic there? Is he really into planning like some of the others?

"No. He likes to pay because he’s a douchebag. I dated him seriously the first few months I moved to Chicago. We’d break up and get back together, break up and get back together, and I finally just had a moment where I was like, you have lied to me and I think you’ve cheated, and I can never go back to being your girlfriend. I’m trying not to let it become something that blows up terribly because he literally knows everyone in the restaurant industry here. I’ve gone on dates and he’ll see photos of me out because he has friends everywhere."

In your Money Diary, you wrote that you were in an Uber after a date and it picked up one of Dave's coworkers.

"Yeah. That was terrible. And we do whatever he wants to do on dates because when I do meet up with him now, it’s literally that I'll maybe get a drink, I’ll spend the night, and then I’ll come home. I don’t have any expectations of that relationship anymore and I am actively dating again. So, when he's like, 'Hey, I’m going to be here doing this. Do you want to meet up?' I’ll say, 'Sure. Whatever.'

"Ironically, the ideal date I described was with him — where we went bar hopping and met his friends. But it’s devolved from really good dates to meeting up while I watch him play pool and play around on Tinder because he doesn’t talk to me. Then we go home and sleep together. It's not the healthiest one of them all — there are a couple that are really screwy — but it works for what it is."
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You went on 20 dates over 30 days and spent $74. Did either of those numbers surprise you?

"It’s pretty normal for me. Twenty is high in terms of the number of dates I’ve been on in a month, but I probably go on at least 10 or 12. The spending is pretty average, as a lot of the dates are drink dates or drinks and appetizers.

"I asked a guy (who wanted to make sure we were platonic from the get-go) what his feelings were on this kind of thing, and he said he likes to do drinks and appetizers. He knows he won't spend a lot, but he still has the opportunity to pick up the tab if it’s going well. He said: 'I don’t expect anything, but I like to feel like I treated her because she gave me her time and she didn’t have to. I just don’t want to sit down to a five-course dinner and discover I hate her in the first 30 seconds.' I was like, yeah, dude. I feel that; makes sense to me."

Are you hoping to whittle them down at all, or continue to date at this pace?

"By tracking, I discovered that part of me does enjoy being single. I loved being married and I loved my ex-husband very much, so I definitely want to get married again. And because I am saying it’s the Year of Yes, I think I'll be saying yes to a relationship versus yes to dating multiple guys."

What did you learn from this exercise of tracking dating expenses?

"It made me very aware of the type of guys I do or don’t date. It’s funny because I don’t like going on fancy dates where guys drop a lot of money because that makes me uncomfortable, but I look back and see it’s an interesting dynamic.

"I’m really happy with all the dates in general — there’s only one I wouldn’t go on again — and when I look at the guys I gave second dates to, there’s no correlation [to money], whatsoever. I’m going to go out with the person on Date #14 again. He spent about $100, even though I very aggressively tried to pay my half because I didn’t want him to feel obligated. I’m also going on a second date with the guy from Date #13, and someone else who spent about $35. Tracking helped me realize what my feelings were for each person."

*Names have been changed for anonymity.
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