Somewhat recently, I recall a rather notable personal finance blogger (happily married, of course) ranting on Twitter about not wanting to see dating advice on personal finance blogs.  I vehemently disagree with this mindset!  I think it would be fantastic if PF bloggers, particularly those who have found some dating success during the age of highly competitive, low attention span dating apps, shared their knowledge for the rest of us sad single people who happen to have an awkward enthusiasm for personal finance and have had trouble seeking a long term connection.

You can’t really look at your money in a vacuum anyway. Money and life are interconnected in so many ways. In my case, money management is something that has been natural and a lot of aspects of it are second nature to me. Dating? Learning how to successfully do that is akin to learning a foreign language. Right down to the aftermath. That is, the more time I take off from dating, the more I seem to forget about the lessons that I’ve learned along the way. I actually went on a date this past Thursday. If you’re not interested in reading my dating thoughts, you can check out the much more accessible “bonus post” that I quietly published last Friday regarding leaving money on the table.

I honestly wasn’t expecting to go on any dates in between now and the start of the road trip.

However, I signed up for what feels like the 14th or 15th attempt at back in June of this year.  There’s still a couple months left on that subscription. Shortly after the time I made the Road Trip Announcement, I basically trimmed the majority of my dating profile. The photos are still there. So are some of the interests. But my dating profile right now? It basically says: “I’m not really dating right now. I’m leaving California on a road trip in March and I’m not sure when I’ll be coming back”. I never expected anyone to be interested in dating me after reading this profile. Periodically, I’ll look at the new subscribers on the website and send some feeler messages out.

Somehow, I convinced a woman to go out with me even with this terrible dating profile.

I’m not even sure that I’m in a psychological state where I can realistically add a woman into my life, but she said yes, she was down to meet me despite my plans to temporarily say adios to my career in 5 months. Anyone who is wiling to do that is worth having an in-person conversation with, right?

Somehow, I convinced this woman that the ideal first date should be something simple.

Staring down someone new at a bar or restaurant is a super awkward social scenario for this introvert. The day turned out to be hot as hell. So we actually ended up sitting on a park bench. And talked. FOR AN HOUR AND A HALF.

We even had a lot of in common.

We’re both outdoorsy, but not the “overnight hikes with tents and gear in your backpack in the wilderness” type of outdoorsy. We’re outdoorsy in the sense that we like staying in a cabin with a mattress, bathrooms and showers. We like going on a day hike and then coming back to the creature comforts at the end of the day. We don’t mind unpacking the tent out of our car on a campground with bathrooms and showers, preferably somewhere near a lake or an ocean. In other words, we’re outdoorsy, but we’re not super hardcore about it.

That’s been a struggle with my dating life (and this woman’s too, as it turned out), because when we mention liking the outdoors on our dating profiles, many of the people who have an outdoorsy interest take outdoorsy to a whole different level that I’ve personally never experienced. This woman did an overnight trek once and she doesn’t have much interest in doing that sort of thing again. I’d be down to try an overnight trek. However, meeting someone who is also at a a TJ level of outdoorsy felt a little bit like hitting the jackpot! Because I’ve never experienced that shared trait before.

She even had a Toyota which seemed to go along rather nicely with my Honda. We both enjoy having a fitness instructor tell us what to do because that working out thing just isn’t going to happen on it’s own.

I very briefly considered truncating the road trip.

We seemed SO compatible for a first conversation, that I started to question the intended length of the road trip because of the possibility of meeting someone locally with potential. And that sort of scared me a little. Here I am, embarking on a huge life change, but I’ll let one hour and a half of conversation influence the duration of an epic road trip? To be fair, that’s one of the things she asked me before we met. And I wasn’t sure how to answer that question.

First, I don’t want to give off the impression that I’m A.) Loaded or B.) Have a cavalier approach to spending money. In addition, because the length of the road trip continues to be somewhat open-ended, I’m just not sure. However, if I did meet someone awesome and it felt like it had the potential to be a long term thing, I assume that I very much would desire to reduce the time spent on the road…so that I could pursue said relationship.

I received the dreaded long-winded rejection multi-text the following morning.

It’s almost always a variation of the same text message. Is there like a blog with tips of how to dump a guy?  “I don’t think we should go out again. Didn’t feel a spark. I really wanted to because you’re such a nice guy and we have a lot in common, but I didn’t.” And, of course, they ALWAYS throw in some variation of “You’re a great guy and I am confident that you will make some woman happy” at the end of their schpiel. This is usually around the time when you start wondering why you are such a failure and if you really were so great and nice, why this seemingly kind and levelheaded person wants absolutely nothing to do with you after all. But, in this particular case, not a whole lot of emotional energies were invested. No harm no foul.

Direct communication about your desires goes a long way in two people feeling “the spark”.

My Spring Fling in April told me that she appreciates chivalry. I asked her what chivalry meant to her. Everyone has a different opinion. I’m not a mind reader. So she told me. And of course I showed up with flowers on our first date (and every subsequent date thereafter). I actually loved that whole experience.  The “extra money” spent is not what I remember about it, it’s the gentlemanly romantic feelings that she enabled and encouraged. The text messages that she sent me during the week about how the flowers made her smile.

It probably also helped that we were pretty open about money and life goals from the get go. We didn’t share balance sheets, but we shared a lot. She liked the idea of retiring early, but her timeline was so much more complex with a company pension and retiree health care benefits. She out-earned me but spent quite a bit less, when you took away her mortgage and my rent.  The flowers and door-opening and such really helped set the tone that this was actually going to be a romantic experience. It also invoked a feeling of mutual trust with each other.

She loved it, I loved it and it was definitely the most fun I’ve had with a woman even if it ended up being only a fling in the end. She even got me to dance. Photographic evidence below. A rare accomplishment. I don’t typically dance. Or wear ties.


Dancing at Gala

This was a weird connection. There were many conversations about the long term even if the connection was short-lived. What would our lives look like if we moved to Texas where her family lived?  Did we want to travel to Big Sur together? She won a free weekend package or something. I wouldn’t need much arm twisting!

I’ve tried to duplicate that chivalrous experience, but most of the women who agree to go out on dates with me have the more common cautious female mentality of “I don’t know you, you don’t get to pick me up at my house yet.” Ugh. I completely get it, but it’s hard to go back after this other experience that felt so different and so positive.

Here you had two people with above median California income. However, for four consecutive weekend dates, three of which were overnight, we probably spent no more than $300 combined. And that’s probably a high estimate. Because most of our shared meals were cooked by us and most of our dates were spent doing things that did not cost either of us a lot of money. While she was a big fan of buying things on sale, one of those meals was duck. Duck from Whole Foods isn’t cheap.  😀

  • Sunset picnic at the beach (she navigated me to free parking. And gave me a guided tour of her city because she knew I’d never been there. <3)
  • A gala for her work (thank you employer of woman I was dating for the free appetizers and alcohol.)
  • Hanging out at her condo. (My funds went towards gas to get there and flowers, while she paid for the food when we went grocery shopping together. You guys, grocery shopping can totally be romantic. Just be observant and use common sense. Anticipate when the woman of your dreams needs baggies when she’s eyeing vegetables and fruits without having to ask you first.)
  • I did splurge for some Saturday Morning rental kayaks on our 2nd date…which quickly also turned into lunch out (while drinking free water), dinner in…and brunch and dinner in the next day! When your 2nd date lasts like 36 hours and incorporates four meals, you probably enjoy each other’s company!?

I think what was huge was that we both agreed that you don’t need to spend a shit ton of money to have a good time just because you happen to have a good paying job. There is so much pressure as a high-earner to spoil a partner with cash. We also both clearly believed that you don’t need to spend money to prove that you care for the other person. Having all those home-cooked meals made me feel super appreciated. Only other women who have cooked for me is my mother and my sister. And I know that me driving us around and helping her out in the kitchen was appreciated by her. Unfortunately, I’m at a loss as to how to express looking for those things in a socially acceptable way.

Of course, it also meant her rejection was an incredibly difficult pill to swallow. She never really gave me a reason for why it wasn’t working for her. And she didn’t have to. It would have been nice to know because I spent more time with her in a month than all the other women in my life combined. I definitely have my suspicions. On our last date, she said that her biggest dream in life was to have her own family. My response on that topic equated to a whole bunch of waffling around and quickly changing the topic. I probably would have interpreted that behavior as a red flag if I was intentionally looking for a co-parent.

Plus, in between the last date and the text message rejection, was an hour long phone call. After hearing about something that happened at work that might affect her year-end compensation; in my infinite wisdom, all I had to offer up was the idiotic “well, it’s a good thing you live on so much less than you earn, right?”As if losing a bonus is going to be no big deal to basically anybody anywhere on the planet.

Nevertheless, I couldn’t stop thinking about how I royally effed it up with the whole kids conversation. That’s always been a “well, maybe If I meet the right person, I’ll think about it”.  I’ve always felt a lot of anxiety about needing to take on the provider role. Because I grew up with such a blessed childhood and my college degree and career choices have not been conducive for paying that lifestyle forward. Unfortunately, I did not open up about any of that with her.

The point of all this is that a lot of people think that you can’t work towards financial independence as a single person and still have a dating life. Dating is expensive right? Well, it doesn’t need to derail your financial or other life goals. If you embark on a more expensive lifestyle when you are first dating, you’re setting the tone with how you spend money. It seems like the key is to find someone who accepts you for who you are and supports your (money or non-money) choices. It certainly helps when they have a similar approach to money. But with high-earning low-spenders being such a small percentage of the population, is it realistic to plan/look for that? I’m obviously still figuring that out.

Readers, what are your thoughts on “the spark”?  Have you ever felt it? Did it last? Any helpful tips to improve my horrific dating track record?

Dating While Saving For Financial Independence