My First Cheap Date: Fail

Day 42 | $31,450 paid | $59,267 till freedom

I met Lindsay for bagels this afternoon and I have mixed feelings about how it went. On the one hand, I initially enjoyed the low-speed, chilled-out approach, and I felt I got to know her really well. On the other hand, she didn’t seem to be as big a fan of the situation as I.

Nancy gave me some solid advice on this whole dating thing today. Her comment to my recent post is worth re-posting, as she made a powerful connection:

Thank you for such an insightful post. I think you should apply the mind of the beginner to your ideas about dating. In your thinking about dating, you are an expert: you have certain ideas about what a woman wants from you or how to show her a good time. Erase those ideas. I think that when you date someone you should be yourself: the person you will be when she is your girlfriend. That way you can truly see if you are compatible and will be happy in the long-term. My husband and I are fundamentally best friends. I think that’s the key. A lot of my friends are dating ideas of people they want to be with (not really seeing their partner beyond the persona) and are, in turn, acting like the person they want people to think they are. This is not sustainable. It is more difficult to be vulnerable and be yourself and not hide behind the formula of fancy dates and shallow experiences. You are clearly a strong and creative person. Find your likeness and grow together.

She gave me a lot to chew on with her comments, and I’m still marinating on it and letting it soak in; I haven’t fully internalized it yet. Thank you, Nancy.

Nancy reminded me of a lecture in another Zen booked titled Not Always So by Shunryu Suzuki. It’s a compilation of his lecture series that he gave at a temple in California. In a lecture he gave on 7/20/69, the same day as our country’s first manned mission to the moon, he talks about how this historical event relates to Zen. Excerpts below:

The first one to arrive on the moon may be very proud of his achievement, but I do not think he is a great hero. Instead of seeking for some success in the objective world, we try to experience the everyday moments of our life more deeply. That is the purpose of zazen.

One time Marian [Derby] showed me some sand. When she gave it to me, she said, “These are very interesting stones.” It just looked like sand, but she asked me to look through a magnifying glass. Then those small stones were as interesting as the stones I have in my office. The stones in my office are bigger, but under the glass the sand was quite similar.

If you say, “This is a rock from the moon,” you will be very much interested in it. Actually, I don’t think there is a great difference between rocks we have on earth and those on the moon. So if you want to find something interesting, instead of hopping around the universe like this, enjoy your life in every moment, observe what you have now, and truly live in your surroundings.

Yesterday I went to visit an island owned by the Nature Conservancy where there are many kinds of animals, birds, and fish. It was a very interesting place. If you live in an area like that and really start to see things, to see the plants and animals in that area, you may want to stay there your whole life. It is such an interesting place. But we human beings go hopping around, ignoring many interesting things. We may even travel to the moon or beyond. It is rather foolish. If you stay in one place, you can enjoy your life completely. That is a more human life.

When we go to the moon I am not sure we are following the best direction for human beings. I don’t know what we are doing.

In meditation, we sometimes practice counting our breath. To count each breath is to breathe with our whole mind and body. We count each number with the power of the whole universe. So when you really experience counting your breath, you will have deep gratitude, more than if you arrived on the moon. You will not be so interested in something just because it is considered great, or uninterested in something usually considered to be small.

Still you may be very interested in having new experiences the way a baby is. A baby has the same basic attitude of interest toward all things. If you watch her, she will always be enjoying her life. We adults mostly are caught by our preconceived ideas. We are not completely free from the objective world, because we are not one with the objective world.

It’s easy to say that Shunryu’s negative view of space travel is ignorant and narrow-minded. After all, beating Russia to the moon gave our country a huge morale boost, and space exploration has contributed many valuable technological advances to society. But considering his opinion from another point of view, through the lens of a Buddhist, it’s clear that patriotism and technology don’t play significant roles whatsoever in the life of a Buddhist, and that he couldn’t care less about something that boosts a nation’s pride or advances technology.

I’m not a Buddhist, so it’s difficult for me to routinely look through this lens, but it’s easy to see one thing that his philosophy can apply to: dates. They don’t have to be huge affairs. Today, Lindsay and I got bagels and coffee. Actually, she got a coffee, I got some OJ, water, and a bagel. She offered to pay for her coffee, and even put a few dollars on the counter when I refused to accept them in my hand, but I picked them up and put them in her purse. We parked ourselves at a table outside to enjoy the relatively cool weather and talked for two solid hours. We laughed a lot, we got to know each other, and it definitely didn’t feel like two hours.

A typical first date for me used to be drinks and dinner then bar-hopping and dancing. It was expensive. Comparing that to today’s date is a little like comparing a trip to the moon to a trip to the Nature Conservancy–the two are completely different speeds and price points. Regardless of which type of date it is, a date ultimately serves two purposes: first, to have fun, and second, to get to know the girl. In terms of the second goal, I would say that I probably got to know Lindsay better than I would have had we done a “moon” date. With dinner and drinks and bar-hopping, there are a lot of seo company distractions. Today, there were considerably fewer. As Nancy put it, “<On a cheap date>, it is more difficult to be vulnerable and be yourself and not hide behind the formula of fancy dates and shallow experiences.”

As far as the “having fun” objective goes, I was actually enjoying myself until Lindsay started dropping bombs about three quarters of the way through the date. We had started talking about the subject of dating, and she told me that she was looking for somebody between 34 to 38 years old. I’m 28, and so is she. That was super awkward, and her remark just sort of hung in the air for a few seconds. She also admitted she was dating a doctor, but she qualified it by saying that things probably wouldn’t work out with him.

I guess this lands me squarely in the friend category? Maybe this wasn’t even a date to begin with? Maybe I need to revert to fancy dates and shallow experiences? I’m completely confused.

Either way, I’m not sure if I’m feeling her either, so I’m not exactly going to cry my eyes out over it. She’s a cool chick,  but I don’t know…she told me that she eats out for every meal since she doesn’t cook, so that shot up some huge, bright red flags blowing in the strong breezes of caution. Not because I want a girlfriend who can cook, but because she’s practicing a flipping expensive little habit, and believe it or not, I’m actually looking for the value of frugality in a woman I date.

Oh, well. It was a good trial run, anyway. We’ll see if I ever work up the courage to ask somebody I don’t know out on a super-cheap date. I think the challenge will be making something out of nothing–finding the sand that looks beautiful under a magnifying glass. Finding the sand and finding the girl to appreciate that sand will take considerably more effort than dropping $150 on dinner and drinks.

Maybe that’s the point.


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35 responses to “My First Cheap Date: Fail

  1. That date was a complete success: you spent $10 to learn this wasn’t this right person for you. I’d say you got a great deal.

    This was exactly what a first date was supposed to be. Save the $150 nights for your one-year anniversary dates.

  2. Jenny

    Please don’t feel like you should be dropping $150 for the night to be a proper date. In fact, there are some girls that might leave a $150 date wondering whether you have problems managing your spending. (Since I typically make more than the men I date, if I see reckless spending I worry the guy would spend my money that way in the future.)

  3. Ron

    Just caught up on the recent posts, here are my consolidated comments / reactions to you discussions of dating…

    For first dates I *STRONGLY* recommend that anyone (rich, poor or on a budget) NOT go for the extravagant $150 dinner, drinks, etc. for a first date. I have come to this conclusion for several reasons:

    1. First dates are like screening interviews. You met a girl that piqued your interest for some small, probably superficial reason. You exchanged numbers, sure, but does that mean you want to commit a block of 3-5 hours of your time and a bunch of money to somebody who might just grate on your nerves after 5 minutes?

    2. There is so much awkwardness / distraction involved in a sit-down dinner & a movie-type first dates that really doesn’t allow for natural interaction or getting to know each other.

    3. Even if you could buy her temporary affection, you shouldn’t. With any worth-while girl you can’t.

    I’ve had girls ask me to buy them drinks when I first meet them and the discussion normally goes something like this.
    Her: “Buy me a drink =)”
    Me: “Oh, a gold digger. That’s attractive!”
    Her: “Pretty please? 😉 ;)”
    Me: “You wouldn’t respect me if I did.”
    Her: “You’re probably right.”

    This line of thought has ended in some interesting conversations with smart girls and this has also ended poorly with girls who were using me. My point is that if her affection was contingent on you buying her shit upfront, then she doesn’t respect you and is just using you.

    4. Some of the previous commenters already echoed my beliefs that if she has a problem with a coffee date / getting to know you, then she isn’t the person for you.

    So what do I recommend for first dates?

    15 minute coffee dates, or the equivalent. If it goes well, then you always have the option to extend it or schedule another meetup. Have a backup plan. Meet for coffee and if you like her, remember half-way through that your favorite bar/park/walk/burrito stand/whatever is around the corner. This also will increase your chances that she says yes to the first date in the first place. If she is not sure about you at first, asking her on a 3-5 hour date can be overwhelming and put too much pressure on her.

    If it doesn’t go well, then that’s just fine. Nobody has invested too much at that point and you both have an easy out. (Good chatting with you, busy, gotta go.)

    Ultimately just remember that you are a high value person. Remember that she has to work to gain your affection just as hard as you do for hers. Also, showing too much interest too early is creepy.

    Now I’m not saying you aren’t doing well with the chicas. Rather I’m making the argument that expensive first dates are not only unnecessary, but I believe less effective at getting dates, determining compatibility, and hitting it off with a girl than lower investment dates. (And on a related note, yes I probably over-intellectualize certain areas of life.)

    • 1 and 2: totally agree with you. my dates typically start with drinks only, but then it ends up going further because we hit it off and i like having fun…even with a bad date i can make the most out of things and make it work.
      3. duly noted, can’t say i disagree
      4. coffee, drinks, i get it–15 minutes to screen. the problem is the next step where I want to go big. I need to practice self-restraint and 1) be really, really selective regarding the girl and 2) not go high-end for step dos

      • Ron

        One of my favorite second or third date activities is a hike. I love it because it is free / cheap and selects for two traits I look for in women: being up for adventure and at least a little outdoorsy. You could even bring a picnic if you really like her, haha.

        You are an active dude, so some sort of hike or physical activity would be a good inexpensive next step. It gets the blood flowing and of course if it goes well you’ll both need to shower and…

  4. Ron

    As for OK Cupid, whether or not you use the online dating service, there are a couple of resources they have that you should definitely take advantage of if you are even thinking of online dating. The lessons are also probably applicable to real-life dating as well.

    OKCupid Blog
    The blog is perhaps the best available data-driven wealth of knowledge with regard to dating, how people interact with each other, and the conclusions we can draw from it. Granted the context is online dating, which is not necessarily the general population, but they do have massive sample sizes. That and it is written by the founder of the site who is both a lovable stats nerd and hilarious.

    My Best Face
    This was a tool the site owner created as an experiment for one of his blog posts, but I believe it is still functional. Want real data about which of your profile pictures the opposite sex likes the best (and a full breakdown of which type of person liked which photos)? You might be surprised at the results. I recommend reading the corresponding blog articles that break down profile photo characteristics.

    Full disclosure: I’m currently in a relationship and haven’t used OKCupid since last year sometime, but I still find the blog fascinating. I had more misses than hits with online dating, but I suppose I could say the same about real world dating. This is fine though because I didn’t drop $150 on every first date I’ve been on 😛

    In business, and in life, I’m a fan of the Fail Forward motto.

    “Take risks frequently, and be prepared in case the resulting action fails to meet your expectations. Fail forward, and there will be learning from your mistakes along the way.”

  5. Cassie Olson

    There are so many ways to go on a great cheap date, that doesn’t feel like a cheap date. Mini-Golf for example. It may not be the “swanky grown up” thing to do, but so much fun. It gives you a chance to talk and let’s be honest here, who doesn’t like feeling like a kid every now and then? Or going to a driving range, going for a hike. Make dinner at home, go to a park or somewhere else outside and set up a little table, have a friend help you out and hang around until you can go pick the girl up and bring here there. Trust me, having a guy go through that kind of effort is so much better than going to a fancy restaurant! It may sound lame, but if a girl can’t be happy with the simple things in life, then she’s not worth it. If all she wants to do is go to nice places and eat expensive food, that’s clearly what’s important to her. If she’s good with the simple, then she’s in it for you.

    • i love it, that sounds very reassuring. i don’t know why i feel compelled to go big all the time. maybe it’s because of that Blind Date or whatever show on MTV?? those people always went on the most ridiculous, action-packed dates ever. bad influence, i suppose.

  6. Angie

    First of all, stop thinking in terms of a cheap date. Start thinking that its a creative way to have some fun without spending a lot of money. One of the best first dates I had with my boyfriend of 2 years is when we got hot chocolate from a local coffee shop and walked around this outdoor mall area with all of these Christmas decorations. We still talk about that one. We had time to get to know each other.

    Second, I completely agree with Cassie. A girl will be way more appreciative of a guy who puts effort into doing some creative then the standard dinner and drinks. If she doesn’t appreciate those efforts, then you know she is not the right girl for you because values money more than other things, which you clearly do not.

    I encourage you to keep dating. Stop worrying about the fact that you’re trying to save money to do an amazing goal. Take it from someone who has a $150k in law school loans, it is awesome what you are doing and the right person will see that. There are many people who are in debt from school and the sacrifices you are making now will pay off. Frankly, you have the foresight to see that tells me you’re a great catch. If you’re willing to do that to make a better future for yourself then you’re willing to scarfice and work hard in life to make your life richer. Not just richer money wise, but as the buddhist sees it, richer in the experiences you are making.

  7. Sarah L

    “A girl will be way more appreciative of a guy who puts effort into doing some creative then the standard dinner and drinks. If she doesn’t appreciate those efforts, then you know she is not the right girl for you because values money more than other things, which you clearly do not. ”

    YES! As a girl, it means so much more to me when I see guys putting in an effort, not just dropping money. Anyone can spend money. I want to know if you actually are interested in me, not just having a good time with me. Assuming I am an average 20 something year old girl, and listening to what other girls have said in the comments, maybe your notions of what a date should be like is more influenced by society and your guy friends telling you what they think it should be, rather than how a girl actually wants it to be. Maybe you’ve been listening to the wrong dating advice all this time, haha.

    • Haha, man, these comments are so reassuring. I just need to get over it. I feel like in our society, though, a big date is what’s expected. And if she knows I went to Harvard, won’t she get suspiscious when I don’t spend money on her?

      • Sarah L

        Suspicious? No. Curious? Yes. Perfect segue way to discuss your short term and long term goals.

        And to be honest, I think someone else mentioned it, but as an average girl, I would say that I actually prefer something a little more casual and down to earth than a fancy dinner date if I’m just starting to date a guy. There’s a lot less pressure for me. A fancy date seems very intentional and romantic, and I’d rather ease into things first and see if there’s a foundation for a solid friendship before it goes any further. It gives me more time to think it over and see if there’s long-term potential. This way, we don’t get caught up in a doomed relationship just because of physical attraction.

        I think what you’re really frustrated about is that you have these two different aspects of you that are somewhat paradoxical and experiencing a collision of worlds that just happen to be manifesting themselves in your search for a girlfriend.

        1. You really enjoy living large (heavy spending on entertainment) and you want your gf to enjoy the same kind of things/moments with you
        2. You’re extremely goal-oriented and you want someone who can support, understand, encourage and match you in achieving goals and actually want to decrease your dependency on others’ approval of you.

        Neither aspects contradict the other, but It almost seems like you think a girl that will be frugally fun now won’t seem as fun to you when you’re back to your normal routine, and it’s hard to wrap your mind around the fact that a girl could be both.

        If all that is true (and it might not be; those were just my thoughts), then it’s probably accurate that most girls won’t be. But the right girl will be 🙂

        • Oy, this is so deep I don’t even know how to reply. I will say this much: I think you’re on the right track. A lot of this is a matter of self-awareness and how much I actually have. I would say that professionally, I’m doing alright. Matters of the heart? Subpar. I guess, yes, I would be fine with dating a laid back girl right now because I can’t afford to do a lot of fun, exciting things. But am I still going to be into her when I’m ready to start “living large” as you put it? I don’t know.

      • Sarah L

        Sorry, I just read my comment and realized I wasn’t too clear.

        The paradoxical part is that you love to spend extravagantly on entertainment, but you’re not because of NMHD

  8. ...

    My Bf is an I-banker and all we do is big expensive dates, I wish he would show a bit more creativity though. I sometimes wonder if he did, if I would be as into him. Sigh, there is a balance strike it for yourself and your future girl, it can work.

    P.S. Lindsay, sounds special :).

  9. ...

    Lifestyle is key, do you know what you want in your next serious gf? I go back and forth between what I have now and having a kick ass Renaissance man. I can’t deny I like balling and I def like when a man does it, doesnt meant that I recognize that it doesn’t mean anything long term.

  10. Sarah

    You live in Austin, spending $150 on a date (unless it’s your anniversary) is a huge waste of money. I’d be weirded out and think, “wow, this Harvard MBA sucks at managing his money.” which is a huge turnoff. Also I’d be self conscious that you would be expecting something at the end of the night.

  11. Hey, fair feedback; point taken.

  12. I’ve been on dates to super fancy restaurants and to super fancy bars. But you know what? The point of dates is to get to know someone and to find out if you want to spend more time with them.

    My general preference is a shorter first date with a clear ending. Coffee is a great first date or lunch if I already know the person somewhat. Dinner is a bigger initial commitment – I could be spending that time with friends instead.

    I may have a high income, but if it feels like someone is trying to spend a ton of money on me, I wouldn’t go on another date with them. Why? That’s simply not how I spend my money.

    Some of my best dates:
    * Late lunch at a cafe near campus (due to class schedules), walking around for a bit. Time constraint was a meeting on his side, which was good – kept the date short, which is important on first dates. I often find that I don’t have a dislike/like vote on a guy’s personality after a first date, so I prefer a longer second date.
    * I love long second dates. Dinner and an activity. Checking out the public market? Ferry to get ice cream? Checking out the beach or some great walking trails? Trying out a sport? Kayaking, rock climbing, hiking? Watching a football, hockey, or baseball game? If you go to a minor league game, tickets might not be that expensive. Cool donut or coffee shops or bakeries?
    * If you’re going to “just” do dinner, take them to a neighborhood they might not have been to before. My city has a ton of cool neighborhoods. I’ve lived here for awhile and I kept going on dates with guys who hadn’t, so I loved showing them around my favorite parts of the city. Sometimes just walking around randomly and then settling for coffee or something can be nice too.
    * I really prefer no alcohol on the first date. That might be contrary to your ideas, but I don’t date big drinkers as I’m not one myself, so someone who doesn’t drink on the first date is a good start.
    * There are so many inexpensive things that you can do outside and have fun, especially when it’s nice out – isn’t it always nice out in Texas?! That’s why I LOVE dating in the summer. Saturday afternoon dates, pretending you’re tourists are awesome.

    At this point, I have a TON of “favorite” date places in my city. I seem to go on dates with guys who lack date planning skills (they should totally teach that in college!), so this is as good skill for me to have (or maybe as Kevin says in the comments on the post I linked to below, I should be dating other guys).

    I also really liked Kevin’s description of his first date with his girlfriend TAG:

    Are you going to go back to your pre-challenge dating ways or somewhere in between?

    • Leigh, thanks for taking the time to write such a thoughtful comment. I’ve done some dating in the past few weeks–couple of drink dates, an ice cream date, a late-night cheese and cracker and wine picnic at the pond near my house, a few hours rowing a canoe around Town Lake (we jumped off the Lamar Bridge a few times then pulled up next to Auditorium Shores and listed to the music coming from Reggae Fest), a few hours at Barton Springs followed by pizza at Home Slice and a tour of the Lone Star Round-Up (hot rod car show on Congress Ave), a few hours chilling out at an apartment pool followed by a super casual Sunday evening dinner at Wich Wich. So, yeah, totally taking advantage of the Texas weather; the pasty white winter skin is being eradicated 🙂 And no, not really going back to my pre-challenge dating ways. This is way more fun and not as expensive.

      I totally agree with you on the activity front–I don’t even really like dinner dates, so the activity thing is definitely more my style. I think you learn as much if not more about a person when you see them in action–talk the talk vs. walk the walk kind of thing.

      I checked out Kevin’s write-up as well as his video. AWESOME. That dude knows what’s up. I am going to use your comments and a resource for further dating. Thanks again!!

      • Ice cream date? That definitely means it’s summer! I love dating in the summer – so many choices of great activities to do.

        Those pretty much all sound like awesome dates 🙂 But wow, that’s a lot of them! I’m pretty sure you’ve been on more dates in the last few weeks by that list than I have in the last TWO YEARS. How do you meet that many new people?

        • haha, really?? all but one of the dates were with two girls…trying to make a decision…which I arrived at on Sunday. 🙂 but anyway, it’s not like each date was with a different girl, so there are no special meeting secrets 😉

  13. Erin

    I was new to OKC and I had my first in-person encounter two weeks ago. I met the guy at a low-key environmental rally (my idea). It skipped over the awkward “first date” because we were actively participating in something. Also, it was free (always a plus) and related to one of my interests. I think doing something like that allows you to see how the person might fit into what your life is actually like.

    I wish the best of luck to both of us! 🙂

  14. That wasn’t a fail– that was a total SAVE! Hooray for not dropping $200! Hooray for not having to have spent a whole evening with someone who is dedicated to an age of a person than a quality. Who says that, anyway?!

  15. soooooo, i heard you today on dave ramsey and ended up spending the last couple of hours reading through this and that on your blog 🙂 rad!

    gotta weigh in on this dating thing…

    if you want a successful relationship a number of things need to be aligned and one of those things is money. my guy and i have been together for 18 years. we have a joint account for bills (which we split) plus separate accounts for “our own money”. we are both cheap but i do splurge on certain things. he is fruuuuuuuuugal. as in, omg would you just buy that instead of looking at it 17 times, its only $10! he has taught me to be more frugal and i love him for that!

    how do you think we would be, without a somewhat similar view on $$? prob not happy/together after all this time. i think its important for you to find someone who has $ values similar to yours. finding that girl wont require “impressing her” with all your dollars, yo!

    and really, when you get right down to it, us girls (humans in general, really) want you to pay attention to us, genuinely compliment us, make us laugh, stimulate us intellectually, show thoughtfulness and kindness. none of those things cost a thing! and tons of guys dont do half of those things while out on dates or otherwise.

    you arent your money. you arent your job. you are a living, breathing, unique person that is has a brain and a heart that has needs that extend way farther than anything money can buy. and that brain and heart you have have more value to give than any money you could spend.

    ps-all i can think of when i think of chicks that expect an expensive date is kanye west’s song gold digger. literally in my head this whole time i’m typing 🙂

    pps-you should TOTALLY do your social experiment with a cheap car! 🙂

  16. the frugal guy's wife...

    It’s only a matter of time before you find the right one, being aligned in financial goals/priorities is very important.

    My husband and I celebrate our 20th anniversary this year. One of the things I most liked about him when we first started dating is that he didn’t feel a need to impress me by spending $$. I don’t think he even spent anything on the first few dates – we drove out to the beach, he took me on my first motorcycle ride..Some of the best dates I’d ever had. He’s still a very frugal guy – cheap isn’t the right word at all, though he is often accused of being just that by friends and family. Me? I love him for it. We have three kids (our boys have always shared a bedroom), live a wonderful and full life, have travelled all over the world – never in high season! – (squeezing a family of 5 in European hotel rooms actually *enhanced* our trip, imho), have no debt and a great retirement nest egg.

    Love your blog, btw. Trying to get my high school kids to start reading it, wishful thinking I guess…

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