2 Incomes Are Better than One: How to Online Date For Men

2 Incomes Are Better than One: How to Online Date For Men

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A few months ago, an FI friend confided in me that he was at a little more than $600k at 32.

“That’s awesome!”, I said.

He lamented,”Well, if I had a partner, I could be retired. I only really need $500k per person since expenses get reduced when you have two people.”

I hadn’t thought about it that way before. Some FI guys either meet women who aren’t super into it (How to convince your partner to FIRE comes up so often in the FI subreddit), or can’t meet the right woman online. These people are great, funny, sweet people, who maybe just need a little help in their online profile.

This post is for men, mostly because I’ve looked at a ton of profiles and received messages from men. I have no clue what women’s profiles look like or what the messages they send are.


Aim for 6-10 pictures. Quality over quantity, so if it doesn’t add anything, don’t use it. Show at least one body and one face shot. Try taking pictures just before sunset, as that is when the best lighting is.

1). Don’t smile, look mysterious and away from the camera.

2). Take pictures via the iPhone portrait mode or get a friend with a DSLR to take pictures of you. Treat your friend to a meal for taking such nice pictures of you.

3). If you have a nice body, sure you can take a picture with it, but don’t make it douchy. For the love of all that is holy, be at the beach playing volleyball with friends and not at the gym. All in context.

4). Wear presentable clothing. You don’t have to step out in a fancy suit, but wear clothes that aren’t wrinkled, have no stains, and fit well. If none of your clothes fit well, go to your nearest Chinatown where they will work wonders for pretty cheap prices.

5). Try and take pictures while you are traveling or doing an activity. Partying is not an activity.


As a woman, I’d say at least 85 percent of messages I received were less than 3 words, and mostly consisted of “hey, “hi”, and “how are you”.

If I really liked his picture, I’d click into his profile and if I thought it was interesting, I would reply,” Is that all you have? I liked your mentions of X and Y.” See, I look at specific stuff! I like to be equal. Every message I sent to a guy was specific.

I know, I know. This is terrible and I should’ve given everyone an equal chance, but when you get a hundred messages a day, you really don’t have time to read everyone’s profile. No, I’m not a model, I’m a pretty normal looking person. It’s just what happens to girls on dating websites apparently.

As a woman, I would ignore all the “hey”, “hi”, and “how are you” messages otherwise.

So, how should you construct your message?

1). Read their profile. Find something interesting about them. If you can’t find something interesting, then please consider if you’re only messaging them if they’re good looking. Do you think that’s the start of a good relationship? I know, I know, I’m guilty of it sometimes — so ask yourself and save yourself the trouble :). If you can’t string together 2-3 sentences, exit out of the profile. Sure, it will take you more time to write a specific message than a generic one, but your odds of a response and date are probably much higher.

If they are still not responding, consider sprucing up your profile and pictures, or that you are punching above your weight class.

2). Mention something about yourself in response to something on her profile.

3). Figure out an open ended question to ask them. An open ended question doesn’t result in one word answers such as “yes” or “no”. Engage her.

4). Write a few short sentences, DO NOT write a few paragraphs. It will come off a bit daunting. Okcupid recommends 40-90 characters but 2-3 sentences is perfectly fine.


“Hey Alice! Glad to see you’re a Red Sox fan, I am too! I’ve always wanted to get season tickets to their games. How was your last trip to Italy?”

“Hey Rosie! Training for a marathon must be crazy intense! I’ve heard of these cool goo things you eat when you run to not get sugar crashes (insert link). How did you get into running?”


Write a paragraph or two inside each section. This is essentially a resume for why you’d be a great date or boyfriend. Show her what you’re like.

1). Show hints of FI, but in PC terms:

  • “love to cook fresh food” instead of “don’t like going out to eat”
  • “love biking along the waterfront” instead of “I like cheap activities”

2). Stay away from cliches such as “netflix and chill” or “wanderlust”.

3). Are you funny? Good at dry wit or witty banter? Show it in your writing.

4). Do spellcheck and run through your grammar a couple of times. If possible, ask a friend to look it over as you might miss something your eyes are used to.

5). Humble brag a little to seem better than the competition. Make sure you’re being low-key about it though.

Other places to find help

The Okcupid subreddit has a great FAQ and you can link your profile to ask them to critique it. Hopefully after you’ve read the above tips, you won’t have to though!

After FireBear and I got together, I ranted about how men don’t try anymore online in large unbalanced cities. It really wouldn’t be that hard to improve most profiles — and I wondered why men wouldn’t try harder. Maybe it’s like the concept of FI. A lot of people who hear about FI don’t really want to live that lifestyle, but a lot of people who didn’t know about FI just hadn’t heard of it before. So, I know the above things might be obvious things to a woman or some men, but I’m sure it’s not to some and I hope it helps. If even one person finds love through some of the tips above, I’ll be happy:).

I joked about starting a dating consultancy. Maybe when I’m retired. For now, I hope this helps some people. Dating IRL and online are just so different.

Send this along to your friends that could use it! Any good dating stories out there?

Author: Olivia

Olivia worked in finance and wants you to learn the secrets of financial independence. She believes there are so many ways to monetize your life and make money doing the things you're already doing because so many companies offer free money.

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8 thoughts on “2 Incomes Are Better than One: How to Online Date For Men

  1. Haha- this is awesome and hilarious! A FIRE dating site might be a novel idea (additional income stream?) 😉

    My husband and I were both very non-FI until a few years into our marriage, but we were both willing to learn and work together!

    1. Oooh, I have thought of that, but my coding skills are not up to par there and not sure how to fix the gender imbalance on it. Seems r/FI is 75% men so I would expect a similar ratio. Maybe instead of calling it financial independence dating, I could call it frugal dating? Would eliminate the gold diggers? Maybe in a few years this will be a cool side project lol.

      That seems like the best way to do it :)!

  2. Oh this is awesome and hilarious!! I definitely need to send this to our guy friends who complain they can’t find the right gal online! Well done!!!
    I agree – Mrs. Adventure Rich and you are on to something for sure!!! Minimum requirement – must post financial report monthly for public share and swipe left or right abilities. 🎉💃🏼

    1. Hahaha, let me know how it goes! Maybe I have a future job prospect as a dating consultant :). It would be pretty fun to do “makeovers” when I’m retired.

      Omg, this sounds so cool and funny! It reminds me of Chinese dating shows where you show your salary, your house, and your car. They’re pretty funny. I can’t imagine the US having such a dating show. Someone in television should get on it. I’m sure crazy amounts of people would watch. Well, I guess it’s like the bachelor. Just restricted to a 20 minute segment for a group of people at a time!

  3. I met my wife via online dating – Match.com to be specific. I tried to never give out generic “hi” messages, so I talked about her dog and my dog in the first message to her. I guess it was enough to get her attention, because the rest is history!

    1. Maybe I should list out the dating sites in order of people who want long term relationships? If you’re paying for a site, it’s a self-selection of people who are serious about it. If you’re on Tinder… well.

      Proof that non-generic messages work :)! A tiny bit of work is huge when others are putting in no effort at all!

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