How to allocate your time while dating

By | June 13, 2017

This is one of those articles that I was rather hesitant to publish. Who the heck am I to give you advice on relationships? The idea is certifiably laughable. But I’m actively working on bucket list item #44 (fall responsibly in love) and I’m a writer and I write about my experience of the world.

I’ve been doing a wee bit of dating recently for something I call Operation Don’t Die Alone, Please. And by a wee bit, I mean a ridiculous amount. When I arrived in Denver, I implemented all the relationship advice I’d been reading. I joined a bunch of dating websites and asked everyone I met to set me up with their single guy friends. I went to a bar by myself with a book and smiled at guys I thought were cute. Okay, I haven’t done that last suggestion yet because I’m chicken, but it’s on my Denver Bucket List, so perhaps I will at some point.

Which aunt do you think she likes better?

My plan of attack was to read a bunch and research and plot and strategize first. I did that for probably way too long. Now I’m staying in one place for a bit and actually, um, dating.

Online Dating

According to Patti Stanger, author of Millionaire Matchmaker, 1/3 of your time should be spent on internet dating. It’s like smiling at a guy in a bar you think is cute, but safer-ish. I tried a few sites and wrote down what I thought.

Tinder and Bumble

I know the swiping apps are all the rage these days, but these were by far the worst of the worst for me. A couple of sentences and a couple of pictures? That’s it? I’m staying in one place looking for depth and these apps felt so shallow. Plus, it’s only available on your phone and I really hate being on my phone. It is shockingly easy to get dates on these apps, but I hated every part of the process leading up to the date.


Completely dead.


Not available for Android.


Easily my favorite of the ones that I tried. A little bit of substance in the bio to gauge my top five must-haves. I tried the “premium” service for a while and that was great. You see who liked you and can target your messages from there. You can also see if someone read your email.

Advice to suitors

  1. In a first message, don’t address me as beautiful, gorgeous, sweetie, cutie, princess or any other pet name. It feels gross and condescending from a stranger.
  2. I promise you that you will never get a reply from me with only “hi.” Even though “hey” is a whole letter longer, that still won’t do. My absolute least favorite greeting? “hru?”
  3. I can tell when the message is a copy+paste. Even if you think you’re being clever, I promise you I can tell. And so can everyone else you’ve sent that message to.
  4. As unfair as this is to say, people stop being individuals after a while. It’s just a never-ending stream of likes and messages. Find a way to stand out. Be funny. Show that you’ve read my profile and you think we would actually be a good match. You get out of what you put into it. Yes, it takes a lot of time and effort to write a thoughtful, personalized message, but it’s the price you pay for a thoughtful, personalized relationship, no?
  5. If the object of your affection replies, offer to meet within the next couple of messages. Nobody wants another penpal.

Out in the real world

Online dating can be exhausting, so I’m glad that Patti had other suggestions. She recommended a third of your dates come from real world interactions – hence the smiling at the bar suggestion.

Let me say now that I know my experience of the world perhaps isn’t normal. I’m a woman. I’m told regularly that I’m easy on the eyes. At under five feet tall, I’m not intimidating. I’m frequently by myself and, perhaps most importantly, I’m a generally happy person and find myself smiling a lot.

All of which is to say that I’m approached and asked out by strangers more than you would think. I counted and in the span of two months (April-May 2017), I was outright asked out — “can I have your number? want to get a drink with me? what are you doing tonight? here’s my card, text me” — seven times in this manner. Walking the dogs. Waiting for the bus. Uber and Lyft drivers. At bars waiting for my buddy.

I feel weird telling you this as I’m not trying to brag — I’m more than acutely aware that my looks are only on loan to me for a brief period. I’m telling you this to set the scene. Frankly, more often than not, I find these interactions incredibly uncomfortable. Occasionally, I find it downright scary. Sometimes I find it flattering. Rarely do I accept.

So I wasn’t fond of this route either.

Friends of friends

Spend the final third of your energy harassing your friends to set you up. These were always the dates I was most excited about. Guys that were already vetted by people that I’ve vetted.

A while back I tried to persuade you that finding a mate was a logical game that you could play with intention and strategy. To recap, you assign every potential mate you meet a number from 1 – 100. The higher the number you assign, the better the match you think they are. The goal is to end up with the highest number possible. You play the mate logic game by raising your own number and going out and meeting a bunch of people to maximize the numbers you see. You win the mating logic game by settling.

I no longer think it’s about meeting as many people as possible. I think it’s more about meeting people who you would rate highly and who would rate you highly. This is why I liked the more substantive dating sites and friends of friends better.

I also no longer think it’s about settling. It’s about knowing what’s important, what’s really important to you and if you find someone who has that in spades, well, that’s kind of nice to not have to think about the rest.

The problem with this idea is that we’re really bad at knowing what’s important to us and our happiness. I think it has to do with evolution or chemistry or biology or some other branch of science. Probably not geology.

I really like this picture.

What’s important?

Here, according to a Catholic priest in his 80s, are some questions you should ask yourself about your future spouse.

  1. Does he have friends?
  2. What are his friends like?
  3. What do your friends and family think of him?
  4. Does he use money responsibly?
  5. Is he stingy?
  6. Can you run his life?
  7. Does he make demands counter to yours?
  8. Does he have a sense of humor?
  9. Is there a history of divorce in his family?
  10. Did he grow up in an atmosphere of racism or sexism?
  11. Are his goals and deepest beliefs worthy of yours?
  12. Does he possess those character traits that add up to a good human being — the willingness to forgive, praise, be courteous?

I love this list.

Finally, a parting thought because this post is getting long and rambly. Learn how to take rejection. I’ve sent emails on Okcupid (following all my advice on initial messages) and never heard back from the guy. I’ve swiped right and not gotten the corresponding swipe. Guys have stopped responding to me for no discernible reason. I’ve expressed interest in guys and they’ve told me they weren’t interested. That’s okay. That’s part of it. Expect it. This is a good time to assess your character. Be gracious. Let it go. Realize that you and you alone are responsible for your own feelings. Nobody owes you anything. Try again with someone else. Feel excited that you’re capable of being excited about someone and know it will happen again.

44 thoughts on “How to allocate your time while dating

  1. amwickes

    One of the best pieces of relationship advice I’ve ever received was from my aunt–she told me to pay attention to how they treat the women in your family, because that’s exactly how you’ll be treated! I think it’s a good litmus test.

  2. Barb

    I’ve been where you are and I met my future husband when I just got out and did what made ME happy. In my case that was doing volunteer work for an environmental agency and he was doing the same thing. It guaranteed that I met a man with at least some goals in common. For you it might be dancing, hiking, cooking class…whatever moves you. The guys you meet in bars are guys that hang out in bars. Ok for some but definitely not my scene. I am a big fan of being your own glorious self and doing whatever floats your boat and you will attract like minded souls.

    Good luck!

    1. Thriftygal Post author

      That type of thing was also Patti suggested for meeting in the real world. 🙂 Excellent advice!

    2. Andrew

      I’ve also heard that volunteering is a great way to meet like minded people. I must put this into action!

    1. Thriftygal Post author

      Thanks! I thought maybe this was narcissistic drivel, so I was hesitant to publish it. I’m glad you found some value from it!

  3. Marty Jenkins

    I have always wondered why it is thought that Catholic priests — unmarried, celibate, males with rather old-fashioned beliefs on contraception — are experts on marriage.

    1. Thriftygal Post author

      Ha! I think because they do a lot of marriage counseling so they see what works and what doesn’t? It’s almost better as an observer and not a participant.

      1. Luis

        Anita you are very astute in your observation.

        If you want to build on what this priest wrote, read Venerable Arch Bishop Fulton Sheen’s “Three to Get Married:”
        My then girlfriend and I were required to read this book by our priest – a tremendous help to our relationship.

        He also hosted “Life is Worth Living” and you can see the episodes on YouTube.

        Good luck on your noble quest.

        Semper FI,


  4. tt

    We are an old species. throughout time, such doings (dating with a mind to substance) have largely fallen into one of several categories- trust someone with the choice and the derivates thereof- arranged marriages or pairings, friend recommendations etc. Or proximity& trusting yourself, which includes work, gazing across the village green, smiling over a cocktail glass, swiping etc.

    Hybrid solutions of course, abound.

    One offs that don’t seem to fit in the modern world? The kidnapping of brides. 🙂

    Trusting yourself and your instincts probably includes the initial pheromone/symmetry buzz.

    Staying in one place can’t hurt!

    You seem to be in the ‘trusting yourself’ camp. Be patient and keep the sense of humor!

    BTW: here’s a likely pick-up line @ Taco Bell: “Four packets? That’s a lot of hot sauce for such a little lady!” (Groan.)

  5. Jeffrey Perez

    I think the main thing is to remain who you are throughout the process so the true you is always transparent to see. All any one wants is to feel whats real…good or bad.

  6. ThriftyOwlDude

    Thanks, especially for that last paragraph. It can be easier to take the whole process personally. One of my fav authors Mark Manson wrote that rejection is actually a good thing- it’s a means to keep people who are not good for each other apart, ultimately saving time and unnecessary effort on both ends.

    1. Thriftygal Post author

      I’m a big fan of Mark Manson. His writing about his love life in the past made me feel less weird writing about mine.

  7. Brent

    Found my wife on eHarmony. I tried several services, but found her there. We were in our 40’s, so maybe we were old enough to know what we wanted…. i.e. know ourselves. My advice is to try not to take it too seriously and try to enjoy the dates with those you realize are not going to get a second date.
    As my soccer coach used to say……don’t wait for the perfect shot to try and score. Besides, you may need some relationship practice before you’re ready for the big game.

    1. Thriftygal Post author

      Ha! I’ve had more than enough practice at this point, I think. 🙂 I really wanted to go on match and eharmony, but I’ve been told they’re pretty dead these days. :-/

        1. Thriftygal Post author

          Everything is an operation! Operation Enjoy the Crap Out of Denver. Operation Enough: A Guide to Early Retirement for those so inclined. Operation Laundry.

          1. thingsthatsparkjoy

            I love it! Re: Operation. I have called mine when I have them (not always the case, but have done so) – “Projects” Muahahahah

  8. classical_liberal

    I’ve been online and regular dating quite a bit over the past couple of years. Both have their positives and negatives. In online dating, keep in mind men have to send out several messages before getting a response and women have to sift through dozens of messages a day. This creates differing strategies for the sexes. A man with a less than perfect first message, but a pretty good profile otherwise, may be just dealing with some quality/quantity/trying to be original ten times in a row issues, so don’t count him out. For anyone who also reads the MMM forum, there is a great thread called something like, online dating is a full time job. It has great anecdotes and advice from many FIRE’ed or FIRE seeking folks on the subject. Learning from others mistakes is a great time saver!

    Good luck in love, thrifty girl and everyone else!

  9. financeswithpurpose

    Kudos to you for really putting yourself out there! That’s a huge move.

    There’s so much I could say here, as I’ve been on more than a few online dates myself…and have tried everything you’re trying. I’ll throw in a few observations, for whatever it’s worth…. (And I suppose I should add that I’m now happily married.)

    You’re looking to marry, and I like the priests’ ideas. For what it’s worth, you might try Tim Keller’s book Meaning of Marriage. Whether you agree or not with his religious perspective, there’s a lot of wisdom in there about what marriage is like/how it works well, and, by extension, how to approach looking for a spouse (Chapter 4 or 5, I believe). And it’s free to check out at the library, right?

    Ironically, I asked my married friends for wisdom about dating when I dated – you want to ask the folks who’ve succeeded, no, rather than your single friends? But most of it was chance/luck for them, and not a lot of really helpful input, except one thing: they recommended finding someone kind. And I fully agree.

    Also ironically, I, just like you, was extremely excited about my friends setting me up. They did so many times, but, wow, those were some of the worst set ups I experienced. Tip: the best way, I think, is to have friends put you in the right place with someone who’s available where a connection may be made. If it doesn’t, great, if so, great, but the whole awkward blind date thing is largely a waste – not because it’s awkward, but because you can usually tell more by simply hanging out around a person once or twice than by going on a date.

    The online dating thing never yielded much fruit for me – a few brief dating relationships, but no spouse material – but in hindsight, it makes more sense. And I’m still glad I did it: it helped me become a lot more courageous about putting myself out there constantly.

    Dating is strange because you really want a spouse, and marriage is unlike dating: you have to live with the person, you share your innermost thoughts and feelings with them, you’re with a lifelong companion, and it’s like living with a living mirror: he/she knows you at very best *and* your very worst. Looking back, I ended up taking the same perspective I did when I was 15: you want a best friend. We can all seem great for a bit, but who would you *really* want to stick with and stick it out with?

    That should be something you look for…and yet, it’s incredibly hard to find via dating apps, one-offs, and the like, because people (and certainly the men!) will overvalue appearance, wealth, or whatever, and discount qualities that would lead to deep friendship. Shoot, with the internet, dating is a crapshoot anyway: there are a lot of oddballs out there, communication with someone you don’t know at all can be challenging, and so on. And I say that as someone who had generally good experiences with it!

    In the end, I found a spouse in the one place I absolutely refused to look and wouldn’t even consider: at work. I tried to avoid the young attractive lady, but my boss made me connect her with people, and she kept fluttering around, so we eventually became friends. There’s a lot more – and fun details – to the story….maybe I’ll put it in a blog post sometime, ha.

    At any rate, I would do whatever you can to put yourself in places where you’ll strike up great friendships with those of the opposite sex who share some of your deepest values. Maybe it’s the FI/ER meetups (Mr. MMM hosts things out your way, no?), maybe it’s at some law thing, but whatever appeals to you value-wise, that’s where I would put myself.

    Best wishes to you out there – dating is a crazy place, although it does give you some great stories!

  10. zeejaythorne

    When I was dating, I looked at it as an adventure. 45 minutes with a stranger is a small investment and you were either bored, mad, or had a good time. If you were bored, you only lost 45 minutes. The other two options at least make great stories. (I must caveat that I am a lesbian and the safety aspect that women who date men face was not really a concern for me)

    I met my girlfriend at a birthday party for my best friend. It was great. She had good taste in good people and looked cute.

    1. Thriftygal Post author

      I wish I had the same confidence in my coolness! Your opinion is welcomed and appreciated. 🙂

  11. walter

    dear Golddigger, how sure are you that you have not already met and started digging a hole with your Mr. Right a long time ago? someone of your caliber, usually would have magnetically attracted many many suitors in the past, even in your young life. i couldn’t imagine you not occupying a special space in some young man’s heart in the past. perhaps he is shy and you were too education, law school, FI goal oriented to notice? hard to notice when your face is buried in a book, working long hours, & or traipsing the globe. i think you should still consider an open casting call of sorts and just let your friends and family do all the interviews/sifting on your behalf. you can date the prospectives after having passed through the thorough screening process. this can become the topic of your second book.

    1. Thriftygal Post author

      It took me a second to understand the gold-digger reference. 🙂 Depth is where the gold is buried. I already know what I want my second, third and fourth book to be, so that would have to be my fifth.

  12. Melissa Yuan-Innes

    How come no one commented on the snake pic? It’s craziness! How it looks like a belt, you’re wearing glasses, you seem to be in a bathroom–love it!

    Your personal posts are my favourite. Other people can, and do, preach about saving money and investing. But, as someone who found her soul mate in high school, I enjoy hearing about your adventures and wish you well in your dating life.

    My only complaint is that if you find The One in Denver (and it’s a numbers game, so if you’re dating, you’ll be finding), you probably won’t make it to Montreal. Montreal is super fun! Tons of art, fashion, and delicious food, not to mention good-looking people. 😉

    1. Thriftygal Post author

      Thank you!! I love this comment and I love Montreal. I’ll be back! And you’re officially on my spreadsheet of people and places. 🙂

  13. Wtp

    Thought about this a lot and why we bother looking for a love interest. Once the chemical storm that is called “love” has settled there are key needs we can get from a partner:

    1. Sex – more of a need for some than others
    2. Companionship – enjoying experiences together
    3. Affection – cuddles, compliments, tenderness, emotional support
    4. Financial security – living with someone who is earning is much more cost effective
    5. Social acceptance – from family and friends
    6. Procreation – kids
    7. Fun – regular fun and excitement
    8. Sense of purpose – for some people a “relationship” makes them feel fufilled

    Sorry to be so pragmatic but truth is we can get most of these with a wide range of people. Or in fact without a love partner at all. And on the other hand, over time it may be one person simply cannot provide all this, hence why we split up, or worse stay together unhappily.

    I find it freeing to realise that a love partner is great, but not a requisite for happiness.

    1. Sweta

      Do you strongly prefer to date an Indian guy or are you strongly opposed to dating an Indian guy? Most Indian girls I know fit into one of those groups. Just curious if you fit into one of those groups?

      1. Thriftygal Post author

        I don’t have a preference. I’ve dated Indian guys. I’ve dated white guys. It’s the person and not the ethnicity that matters.

  14. Sweta

    The comment above was meant for you, Anita not commenter Wtp.

  15. Laszlo

    Congrats, TG — the idea is in motion with you. Are you familiar with the song “So Happy Together”? Your energy reminds me of that. Notice the frugality?

    If I should call you up, invest a dime
    And you say you belong to me and ease my mind
    Imagine how the world could be, so very fine
    So happy together

  16. shriekster

    From a guys perspective, a huge barrier in online dating is coming up with a witty line to stand out from all the “How’s your day/week/weekend going”, “Hello”s, or even worse, “Hey”s that most guys tend to send out. I’ve done the whole OKCupid, Tinder, Bumble route, and I completely agree with your sentiment on each one! I still think nothing beats meeting someone in person and going from there…with online dating, theres a mild loss of “discovery” since you already have an idea for their interests and aspirations (although perhaps that isn’t a bad thing?).

    Finally, for me, of course I would like to find someone in the “right’ financial mindset. It’s especially hard to know what the opposite person is like while dating in the beginning…how would you even bring up a topic like financial wellbeing without sounding like you’re trying to pry??

    Wish you the best in your search!

    1. Thriftygal Post author

      I think you can kind of gauge if someone has the right financial mindset from their reaction to your retirement plans. 🙂

  17. shriekster

    Haha, fair enough. I guess the only way to find out is just to lay it all on the line


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