On Dating and FIRE

Today I want to talk about a subject that maybe doesn’t get much of a mention in FIRE circles. Yes, that’s right, dating. Other FIRE bloggers out there all seem to be either married, or happily settled down, and so on and all that, and the subject of dating doesn’t get a mention all that often.

So recently I’ve been dating a lot, and I have some questions I’d like to put out there. To give a little background, I broke up from a long term relationship about a year ago (yes yes, sympathy, thank you!), and towards the end of last year and throughout this year I’ve been on a fair few dates. At the venerable age of 32 I’m not getting any younger and I need to, you know, find a girlfriend. My little sister is growing concerned, it’s that serious.

Now, ordinarily this wouldn’t be that noteworthy, but I’m pretty sold on the whole FIRE thing and that does throw some interesting questions into the mix. So here I’m going to try and answer some of those, like some kind of weird agony uncle or something. But I would of course welcome any advice that my many readers (cough cough) have.

How soon should you mention FIRE?

So the first date I went on towards the end of last year was with a girl I met through my writing class. She was/is lovely and we had a good night but, sad to say, she declined the second date (okay, put away the tiny violins). Now there are many reasons why she might have declined the second date, but it perhaps didn’t help that I yabbered on for a short while about my property investment plans and extreme savings rates. When I think about it, that’s not really first date conversation material, is it? Trying to explain the mortgage leveraging principle is not the way to woo a girl.

bored date

I really liked that girl but it wasn’t to be, so I set to putting myself out there a little bit more. I went out on the town a lot at the start of the year, but it turns out I’m not that great at chatting to girls out and about, and so eventually I decided I’d create a profile on a certain dating app (the name of the app rhymes with Lucinda, though I haven’t met any Lucindas on there yet). I put some pictures on there and a little bio, and a few lines down in the bio I wrote something along the lines of: “I have this crazy plan to retire by the age of 40, care to join me?”

I’m sure there will be people with their head in their hands at his point. I’m not sure what I was thinking. The thing is, stating my early retirement plan didn’t stop me getting matches and dates, but I’m not sure it helped either. One girl I went on a few dates with, and on the third date I brought up the subject of early retirement (see I’m learning, I waited three dates before mentioning it). She said: “Oh, wow, I thought that was just a joke. I didn’t realise you were serious.”

(It didn’t work out with that girl. Not because of anything related to FIRE, more because she was absolutely filthy. And not the good kind of filthy. There were other reasons but that was the main one. Sorry to say but her flat was a pigsty. I mean I never thought of myself as particularly bothered by cleanliness, but I’m reconsidering that now. There’s a certain level of hygiene that is necessary right? I mean you shouldn’t find a half drunk bottle of coke next to the bed with mould in it. Or bread crusts in the bed. And your bedroom shouldn’t smell strongly of cat urine…)

friends messy
It was a little bit like that episode of Friends

Anyway, I guess what I have taken from this is that it’s better to hint at such things (FIRE aspirations that is, not filthy bedrooms), but let the details of those aspirations emerge slowly over time. If you need to write a dating profile then mention some of the things you’d like to do one day when you retire – travelling, writing, volunteering – or whatever, but don’t actually say to someone you’ve never met that you want to retire by the age of 40 – there are so many ways that could be misinterpreted. Perhaps they might think you have no ambition, or you’re a layabout. Perhaps they might think you’re difficult or contrarian. Perhaps they might think you’re loopy.

The thing is, most people don’t know what FIRE is or all the technical aspects behind it, and you can’t explain all of that on a first date or in a dating profile. And there’s no way your potential spouse will be convinced straight away – I certainly wasn’t. You have to let the ideas seep in, slowly. The expected things to do in life are get educated, get married, have kids, and work until the usual retirement age. It takes a little while for a potential spouse to consider other options and other ways of life.

Should you consider financial independence when looking for a girl?

I’m going to admit straight away I’m just as shallow as the next guy (and probably most girls too) in that I would like an attractive partner. But you know, I also look for things like common interests, humour, intelligence, kindness perhaps. There are loads of things that make up a person and I don’t expect a girl to be perfect in every way. And hey, as Robin Williams says in that film, it’s the imperfections we fall in love with.

robin williams
She used to fart in her sleep. One night it was so loud it woke the dog up. She woke up and gone like “oh was that you?” I’d say yeah…I didn’t have the heart to tell her…

But once we’re past that initial checklist (for want of a better less clinical word), should we consider things like salary, a good job, saving habits, and financial responsibility?

Now, I don’t necessarily consider these things straight away. They are pretty low on my list of things to consider actually. If she’s in a lot of unsecured debt that might worry me a bit, but there could be good reasons for that so I’d probably give her the benefit of the doubt. I don’t care if a girl has a good job, or her own place, or savings. But, to flip it around, I would say these are quite high on a girl’s list when seeking a guy. I’m generalising horribly I know, not all girls are the same, but I would say most girls want a guy who has it all together – the job, finances, his own place, and so on. Is this unfair? I don’t know, maybe.

I remember watching this film PS I Love You with an ex-girlfriend and there is a character played by Lisa Kudrow who always directly asks three questions of a guy she meets: “Are you single? Are you gay? Are you working?” If the guy doesn’t answer “Yes, No, Yes”, she simply walks away. It’s funny because she’s so direct and wastes no time with awkward niceties. Whereas I’d guess most girls are a bit more subtle about finding out these things. With internet dating these days those three questions are instantly addressed so a girl doesn’t even need to ask. I wonder how many guys lie about their employment status or profession in order to get a date? Quite a few I suspect.

I went on a date with a girl a few months back who had recently been made redundant and still lives with her parents. I knew these things already before I worked up the courage to ask her out – we met through friends on a walk and we’d been chatting throughout the day.

We didn’t go on a second date though. Why? Well it was nothing to do with personal finances, and more because I think she might just have been a little bit crazy.

(It’s not really FIRE related but if you’re interested, here is roughly our text message conversation when I suggested a second date:

Girl: Did you think there was a spark? I didn’t think there was.

Me: I’m not sure if I believe in ‘sparks’ but that’s cool, we can leave it there.

Girl: Yeah I’m not sure about a second date.

Me: No problem, if you have doubt then it’s probably not gonna work.

Girl: Like you seemed embarrassed when you complimented me. I have low esteem so I need someone who is okay to compliment me. I think too I’m looking for someone who is done with nights out in town. I don’t mean any of this in an offence way btw.

Me: It’s cool, you don’t need to give me reasons, we can just be friends.

Girl: Oh, well maybe we could go on a second date and see how it goes.

Me: Okay… Now I’m confused.

Girl: Confused about what?! You wanted a second date! Forget it then.

Me: I just thought you weren’t interested?

She then proceeded to have a big rant at me, saying all men are the same and play games and so on and so on at which point I said something along the lines of “Okay, let’s give it a couple of days and see how we feel.” I never messaged her back. I need to make peace with her because we’ll probably bump into each other at some point – mutual friends and all that – but I’m fairly sure a relationship wouldn’t have worked.)

Anyway the point is, I’m not that bothered about a girl’s financial situation, or her job, or whatever. Which might come as a surprise given how interested I am in personal finance. I guess I’m fairly used to the idea that I’ll be the main provider in any future relationship, and, ultimately, there are other more important things to me.

Should the man always pay on a first date (and/or second date)?

should men pay
Here’s a random sample I found on google

For some reason it seems to be the convention that the guy will always pay for the first date (or two). I guess this is because usually it’s the guy asking the girl out, suggesting the venue and so on, and often the guy is earning more than the girl, so it makes some sort of sense.

But it’s all very confusing, and I don’t like the whole situation really. If a girl insists on paying half should I be offended or pleased? Is it because she’s not interested in taking things further, or is she just trying to pay her share? Is it chivalrous for the man to pay, or is it patronizing, or patriarchal? How expensive or cheap should the restaurant be? If I suggest an expensive restaurant what will the girl think, will she be impressed or feel guilty or indifferent? And so on and so on. It’s all very awkward.

In March this year I took a girl out on a date and we went to this lovely independent Italian restaurant in Northampton. So, the waiter brings us the wine menu, and the girl I’m with casually asks the waiter which wine he would recommend. Nooo! I thought to myself. Don’t do that! He’ll suggest a really expensive one! (Personally I always pick the wine that’s not the cheapest but the next one up if you know what I mean, that’s normal right? Or am I just a cheapskate?). Naturally the waiter didn’t pick a cheap wine. He picked a very expensive wine. They both looked at me, my date and the waiter, and I nodded with a little bit of a grimace. What else could I do?

Part of me thinks that in an equal society both sexes should pay their share, but then I don’t think we do live in an equal society, so generally I’m okay with paying. Unless, say, I knew the girl was earning more than me, or if she was the one that suggested the expensive restaurant, or the expensive wine.Β  I just try not to think about it really.

One thing it does affect is my monthly savings rate! Perhaps it’s not that big a deal, but I do still wince when I hand over my card. I do like to eat out but when I’ve been in a long term relationship with a girl we’ve always found special offers and saved the pricier restaurants for special occasions. So dating feels a little uncomfortable for me – picking out a restaurant because it has a half price deal on is a bit of a no no as it could easily be taken the wrong way.

Should I boast about my financial situation?

Okay the answer is obviously ‘No’. But can I hint in a subtle way that I’m doing very well thank you?

Well firstly, I’m not doing that well. I have friends who are earning ridiculous salaries in London and make me look poor by comparison. Still, and not wishing to boast or anything, I would say I’m doing alright, with my salary, my investments and so on. I’ve paid off my student loan, I have a healthy pension balance, I have a rental property. I’m doing okay.

I guess the implication is, can I use these things to try and bag myself a slightly more desirable partner? The answer? I don’t know but probably not. In any case it’s not a good attitude to have. Someone pointed out to me I might be the target of a gold digger if I wasn’t careful – again, highly unlikely – but it does make you think. It sounds cheesy but I want a girl to like me for who I am, not for my financial prospects. And also I don’t want to find myself losing half my assets in 10 years time to a costly divorce.

Still, I think like I mentioned above, it doesn’t hurt to mention I’m quite responsible with money, that I prefer to save for financial freedom than splash out on an expensive car lease for example. I would hope that this sort of attitude might attract the right sort of girl. That’s not to say that I’m boring or anything, just that I know the value of money, because ultimately money is earned through work, and work wastes time that I could be using to do other, more exciting things.

To try and sum up…

Dating, in my view, is one of those necessary evils. That might sound unromantic but I do believe you can’t really know someone after one date, or by looking at their dating profile. It takes time and effort to get to know someone and develop something meaningful. And there’s a lot of nervousness and awkwardness to start with.

Unfortunately so far I don’t seem to be getting anywhere! Having said that, my sister has just set me up with one of her friends. We met before, at my sister’s wedding about 5 years ago, and got on well. We have a lot of common interests. So maybe that will work out. Randomly she added me on LinkedIn which was a little odd, but it does mean I’ve been able to see her CV which is fairly impressive. So no financial worries there (hopefully)!

Anyway, if anyone is reading this, what do you think? Have you had any dating mishaps or misunderstandings? Oh, and here’s an image I found when I googled ‘dating’ and ‘fire’ together, it seems quite apt:

dating fire

Okay dating is not that bad, but it amused me anyway. As always thanks for reading,



7 thoughts on “On Dating and FIRE

  1. Thanks for sharing this, I posted something about dating 3 years ago and noticed there were hardly any people persuing FIRE who were on the dating scene. I came out of a relationship last year and what with getting a new job etc, I’ve not gone back onto the dating scene. However, if you think it’s tough dating in your 30s, pity me in my 40s! πŸ˜‰

    In my age group, I have to consider if a potential date has children, how many and what age. No, I don’t mind children, but if they’ve all still to go through university, then that person’s finances are going to be pretty tight and therefore not aligned to my own. Divorcees too – don’t have anything against them but there could big holes in their finances from having to pay their exes!

    Financial criteria never used to be an issue with me when choosing a partner but is something I now have to consider for potential dates.

    As well as financial criteria, in my age group, many men have let themselves go, so I also have to consider health/fitness criteria. Since I try to keep myself fit and healthy, it’s only natural that I’ll be looking for similar. Or go for younger guys.

    And no, I don’t think the guy should always pay on the first date – I always offer to go dutch, plus I would never choose an expensive restaurant – too much expectation and pressure there.

    Dating is a minefield. I guess as I’m older, I could probably mention early retirement and be taken semi-seriously – it might be something for you to keep quiet about for now at your age though.

    Anyway, all the best and good luck with the dating!


  2. Interesting thoughts. I’ve always wondered what it would have been like to be on the FIRE bandwagon while still single. I honestly don’t think that I would have latched onto the idea so readily if I wasn’t already “settled down” so to speak, I was a bit of a nightmare in my early twenties! Not with money so much but just with not really giving a shit about what the future might hold… literally no long term plan whatsoever. I didn’t really start thinking about that until Mrs T came on the scene and was like, well this is clearly going somewhere, time to start thinking about the future.

    Loving the bit about the wine, I can imagine I’d be exactly the same…. although beware about choosing the 2nd cheapest wine… I’ve heard they deliberately put the actual cheapest one as the second cheapest on the menu as they know everyone does what you do and go for the second cheapest (and end up with the cheapest although they don’t know it) and therefore maximise their profit margins. May not be true but something to think about next time your out! πŸ™‚

    I used to hate dating and find it as you say very awkward, nervous etc… Although I am sure it’s a lot easier with all the apps around nowadays!

    GL with your search for Mrs Wephway, and sorry I can’t really be much help being a boring old married dude πŸ™‚


    1. Thanks, actually it was one of my exes years ago that would tell me off for not budgeting or having any idea where my money was going, so maybe that’s where it all began. And thanks for the tip about the wine, maybe I will just buy the cheapest in future. Or the third cheapest…


    1. Ha, that sounds hilarious (and very practical too), I would love to read that post! I’ve no idea where you’d even start, perhaps I need more imagination?


  3. Having never dated really before (I met my ex very young) I quite enjoyed dating but I did find the whole financial bit difficult. I met my current girlfriend on my 3rd date and she’s not money orientated at all which is nice and insisted on paying for every other date. She lived in a rented flat and I knew she earned less than me and I also had my lodgers basically paying half my mortgage for me so I decided to be direct about 4 or 5 weeks in to going steady. I said ‘I’m going to ask you a very personal question’ she said OK and I asked her outright what she earned. She was a bit shocked and said that wasn’t what I thought you’d ask! She did tell me and I earn 3 times what she does. I just said look you insist on paying half and that’s great but I worry you’re struggling and if I want to do something like take you to the theatre or out for a meal I want to enjoy it and not feel guilty. So let’s make a deal. I’ll book things and assume I’m going to pay for them m you contribute what you can that’s fine I don’t want to be a meal ticket but I want to enjoy taking us to places and not worry that you are struggling to afford it. It actually worked well. I booked the theatre tickets. She’d pay for the train down there. It’s still complicated now she’s moved in as I own the house. She pays me ‘rent’ and she’s also saving up to buy a %off me so she has a stake long term I will probably do a prenup at some point as I’ve seen too many people ruined by breaking up and I don’t see why I should give my hard earned money to someone because they’ve lived with me. If that makes me un romantic so be it. It’s a conversation we’ve had. I’ve tried to get her interested in saving and she does save but isn’t quite as obsessed as I am which is probably a good thing. Reminds me to have fun too

    Liked by 1 person

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