Reader question #86: Tips for dating brilliant badass women?

Dear Captain Awkward,

I’m just going to jump right in.  I have a first date coming up with a very attractive woman and I am freaking out a bit.  We met on <Dating Website> and I feel like we gave each other really good message.  Over the course of our conversation I learned her first name and the company where she works, which was of course all I needed to Google the shit out of her.  Oh Captain, I normally have anxiety issues in general, but what I found has escalated this to Code Red.  Turns out she went to <Very Snooty All Girls Boarding School in New England> and then attended <Very Prestigous University>.  We work in the same industry, but she works for <Big Time Corporation> in <Iconic Skyscraper That Gets Blown Up in Movies>, and her job description is what essentially would be my boss, if not one level higher than that.  She does tons of awesome charity work.  She has been featured in newspaper articles about “Top 30 Under 30” and “Most Eligible Singles.”  None of this (other than her employer) has been brought up in conversation, only through my Google snooping.
In short, I am not ready for this girl’s jelly.

Don’t get me wrong, I am a smart guy and enjoy my job and life (most of the time), but I feel like she has her shit together way more than I do.  I know she lives in a nicer place than me, makes way more money, etc.  And I know those are bullshit material things and no way to judge a persons worth….but I worry how she is going to look at me when it becomes clear she has accomplished so much more.  As one of my friends said when I was lamenting my “problem” to him – “Maybe she’s really attracted to slovenly oafs?”

I feel like I should mention that she was the one who messaged me first.  Contacting me out of the blue and praising how much my profile made her laugh and wanting to know more about me.  Like I said, our messages have been great and when I asked her out for drinks she quickly accepted.  I realize this is a good sign, but if anything it has made my stupid brain worry more.  Like “There might actually be something here DON’T BLOW IT.”  (or as much “something” there can be after a few dating site emails).

I know you’re just going to tell me to “be myself” and worry more about whether she’s the one cool enough to be with me.  But is there any advice you can give on how to be less of a spaz about this and just let go?

Even The Beast Had An Awesome Castle

Okay, Beast, your letter was so personable and funny that it had me Googling the ethics of an advice columnist asking out someone who writes in for advice (Good news, everyone, there are no rules about that), so I’m pretty sure you’ll do fine.

Snooty girls from New England need love, too.

I know many brilliant badass women who are great at stuff. You’ve all met Commander Logic, yes?  Basically, all of our friends are as awesome as she is.  And they are all unique fabulous creatures and there is no one way to impress them or get to know them, but I can tell you one secret peeve/awesome thing that comes up over and over in discussions of online dating* we’ve had with each other:

  1. A guy who gives good email and then segues into making plans in a way that is effortless, like, want to do something Tuesday? Sure, ok, let’s meet at <place/time>  = SEXY.
  2. A guy who must trade 17 emails in order to make plans, and keeps using the words “Whatever you want to do is fine” and confirming and reconfirming and offers everything a an option, like, “Well, I know we said Saturday but I could also do Sunday OR Tuesday…if you wanted...”= ANNOYING.  Sometimes we rally and go on this date, but it is doomed from the get-go.
  3. I wrote this in 2005, and while I think the section on Cafes I Have Loved is overwrought and pretentious, the premise that The Coffee Date Almost Never Works is basically sound.

So that is my advice for you:  Be able to suggest a solid plan with confidence. If she suggested the plan for the first date, roll with whatever she suggests and have a good time and know that for the second date you’re the one who makes the plan.  No need to go overboard – you’re not Richard Gere taking Julia Roberts to the opera in Pretty Woman – but being able to come up with a cool meeting place that is relaxing to be in and where you can hear each other talk where there is something to look at or do (or that is also walking distance from a restaurant or movie theater or gallery or some other place that you can spend some time if the date is going well) is essential.  Bonus points if it’s some place that you love or have a personal connection to or are really curious about and can explore together.  It’s less about impressing her with how hip you are than about knowing what is a good space for hanging out and connecting and making everything really easy and relaxed.

I feel like a lot of brilliant badass women comment here and will be full of good suggestions for you.  SexyTypewriter, get in here and tell this guy what’s what!


*True story:  There was a year we were pretty much all on <DatingSite> at once and nearly broke the city of Chicago with our awesomeness. Also, if you liked one of us, you liked all of us, so there was much comparing of notes and mocking of triflers.  Long live the Shadowy Dating Juggernaut!

32 thoughts on “Reader question #86: Tips for dating brilliant badass women?

  1. Captain’s dead-on here. Another good thing to remember? It is totally okay to tell the nice girl she is cool – we all like to hear about how pretty and awesome other people think we are. Especially on dates. It is really not sexy to be in a conversation where you tell someone they are super-cool and then go all insecure and start comparing yourself to them. Then that person has to flip into mommy mode and take care of you when we would much rather be in stiletto and cute outfit-wearing mode.

    Why is she attracted to you? You may be the Adler to her Sullivan or the Tracy to her Hepburn. Good partners usually have diverse and complimentary talents. Have fun!

    1. That’s a great point – sometimes when we’re off conquering the world people just assume that we know how cool we are and that it would be redundant to compliment our shining eminences. This is incorrect. “You are smart and pretty!” is never the wrong compliment. Saying “you are so smart and pretty, what could you possibly want with a schlub like me?” is a trip to the friend zone waiting to happen.

  2. I hate to maybe write something obvious, but as a Put Together Smart Girl (though not on that level) dating someone who technically, by school specs, isn’t my education-equal: suck it up. If she likes you, she likes you, and huzzah! If she’s as put together as she comes off to be, then likely, she knows what she wants, and gosh darnit, she contacted you!

    No one would think twice at all if it was a “more put together” guy and a “newbie” gal. Have a good date, and be awesome. Don’t be intimidated–so many men are, and it’s lame. We appreciate guys who rock who they are without getting weird that their lady has more money/education/status than they do. We all have our own quirks and damnit, we’re in the 2010s here folks.

    You said it yourself: you’re smart, you enjoy your life, and she contacted you saying how funny you are and how much she enjoyed your style.

    have a great time!

    1. Yes, this. When I first started dating Mr. Dingo Jones long-distance, people questioned how I could possibly re: (1) education, (2) Texas, and (3) extant offspring.

      Reader, I married him.

      And he is so awesome omg.

  3. The Cap’n is right on. #1, don’t see her as what you googled, ask her about herself and get to know HER. Brilliant badass women need love, too, and you are also brilliant and badass. Just try to put all the googling out of your mind and treat her like another human being who you are trying to get to know. Google doesn’t know anything about her, really.

    #2 Having a plan, ANY PLAN, is sexyawesome kryptonite for brilliant badass women. The cheapness of the date is irrelevant. Tell me to wear tennis shoes ’cause you packed peanut butter and jelly sandwiches for a picnic in your favorite spot in X park? I’m a goner.

    True story, HusbandLogic wooed me by planning a date for us that I was ALREADY GOING TO. See, my OKCupid handle was the title of a song by a relatively obscure musician. HL knew and loved this artist, and this artist was having a concert in our city in the near future, to which every fan of this artist would already have a ticket, including HL. The entirety of his first message to me? “Hey. Where will you be at 8PMish on {date of concert}?” We met up prior to this concert, but the date, time, location, and interest-to-me-personally specificity of his first message? Totally buckled my knees.

    But mostly #1. She is a human, not an assemblage of possibly scary stats. Maybe it’ll work out, maybe it won’t, but just let her be who she is, and tell her when she’s being awesome. No one ever gets tired of hearing that.

  4. Can a lady with a high school diploma have a happy relationship with a guy who has a PHD? Um. YES. So why is it such a problem when the gender roles switch places?

    Letter writer, you seem funny and charming and cool, but listen up: I used to date guys who would be all, “You are so much more interesting/put together/smart/whatever than I” and finally I realized it wasn’t a compliment! It’s an excuse. Do you think she is awesome and badass and attractive and smart? Great. Feel free to tell her those things. Maybe not all at once, though.

    Do you think she’s an idiot? No? Well, then don’t insult her by thinking she is too stupid to realize you’re a loser. Clearly, she thinks you’re worth at least some of her time. Put on a nice shirt and have a good time.

    Don’t put the lady on a pedestal: it’s really hard to stay up there. Famous people have to fart, too.

  5. Laughing at the “famous people have to fart” comment, because my thing was going to be that she still puts her pants on one leg at a time. The farting is much better though.

    When I met my husband I think he had a similar crisis about me, being that I was further in my career, hell, that I actually HAD a career, I made more money than he did, had investments, the whole kit and caboodle.

    What I like about him is that we can have a good time together. I don’t want to talk about my work when I’m not at it, so it’s not something we really need to have in common.

    If she’s so badass in all those Googleable things, she’s probably bad ass enough to not give a shit what you make/don’t make, etc. And she’ll be bad ass enough to understand you might be a little intimidated. If she’s REALLY badass, she’ll think it’s awesome you were honest with her. And your honesty will be a turn on, and sexy fun time might follow. I’m just sayin’.

  6. Captain Awkward, do you have any suggestions for fun things to do in Chicago? I realize this is off topic, but every time you mention Chicago in a post I think, “Captain Awkward is so cool. I bet she knows all of the fun things to do.”

    So if you have any suggestions I’d love to hear them. My friends and I are always looking for interesting ways to spend a day in the city!

    Back on topic, I wonder if Beast has a problem dating women who he considers less successful than him. Because if he doesn’t then he should be able to see that there’s nothing wrong with being the less “successful” one in the relationship. If he’s able to date people with worse jobs or less impressive educations then it stands to reason that the woman he likes should be able to do the same.

    1. As a fellow Chicagoan, I gotta dip in here. Mostly? It’s all about knowing what’s happening in my neighborhood; I’m lucky enough to live in a neighborhood with its own news and events blog. But when I want to go outside the neighborhood, here’s where I check out the scene: (the center column titled “Slow Down” is the best)

      If you’ve got people to show around downtown on the tourist tip, take ’em to the Bean, walk along the river, show ’em the rocks-from-famous-places embedded in the Tribune building, and if they want to go up high, hit the Hancock’s Signature Room for a cocktail. DO NOT go to the observation deck; it costs money, is only a couple floors higher, and has no access to cocktails.

        1. I have a few suggestions, as someone who moved to Chicago 2 months ago and found really, really unexpected good friends…

          Go to places like the Whistler or Hungry Brains or the Hideout or Streetbar or Smoke Daddy or Beauty Bar or Cole’s. Check out their bands and DJs. Then hang around and MEET the musicians. These are people hoping to expand their circle of fans; they are open to chatting and you might be able to make friends with them or with their other fans. From there, it’s a spiral into meeting more and more people. The line “I just moved to town and I’m hoping to meet people” opens a million doors in this city.

          The mixed group Ami Saraiya has a wide variety of musicians in it, all extremely friendly. They play a lot of gigs and introduce people to each other to expand their fan base. And I’m sure any of 50 bands would do the same.

          Chicago is a tremendous place. Tons of arts and movies and music. Just go out there and I think you’ll find the midwest charm is open to making new friends!

    2. Circling back to list places I like in Chicago:

      Uptown Poetry Slam at the Green Mill (Sunday Nights)
      The Hideout
      The Music Box
      The Siskel Center
      Doc Films (I’m a filmmaker, what do you want?)
      Garfield Park Conservatory
      Green City Market, and many neighborhood farmer’s markets
      18th Street in Pilsen for cool coffeehouses, a good grocery store, some neat bars, and ALL the Mexican food
      The Thai & Vietnamese places near the Argyle stop on the Red Line
      90 Miles to Cuba Cafe
      Seeing a cheap matinee at the Davis after lunch at Selmarie in Lincoln Square
      Playing board games at Guthrie’s
      Free Wednesday shows at Improv Olympic
      Seeing a show at the House Theater/Theater Oobleck/Shattered Globe/The Hypocrites/Backstage Theater Co./Babes with Blades

      That’s the tip of the iceberg. I’ve lived here 11 years and am just getting to know this place.

      When I first moved here I did a project where I tried to go to every eL stop, and I also looked in the Reader for cheap/free things to do, so I’d have Friday Adventures.

  7. Captain Awkward : coffee dates :: me : happy hour or any variation of “just getting together for drinks.” But meeting someone for a drink doesn’t have to be stupid boring. If you like beer, suggest a really good tap house and get a taster plate. Same thing if you’re really into wine or cocktails — find a cool boozy event and take her to that and you’ll still have looser tongues than you would if you just met for coffee, but you’ll also have more to think and talk about than you would if you just met up at your favorite bar to drink the same stuff you always drink and try to think of good icebreakers.

    Related: one of the lamest dates I ever went on was with a guy who asked me to meet him at the bar he always hung out and played pinball at, so we could…hang out and play pinball, something I told him I was game for while I admitted I hadn’t played pinball in years and was not that good at it. “Hang out with me while I do exactly what I do every other night of the week, in the exact same place I hang out all the time” is a terrible premise for a date. You should do something you both like and find fun and both be a little bit out of your element — but not too much.

    1. Ooh, or a wine bar that does different tasting menus for guests. There’s one in my town that does flights of just 3 glasses of wine, and the sommelier will only come back and tell you which is which once you’ve tried all of them! Great place for a first date.

    2. I kind of really hate coffee “dates” these days. It’s like…no effort put in, so you don’t have to emotionally put yourself out a teeny bit.

  8. I’d just like to echo a point here: Don’t play the self-abnegation, I-totally-suck card. Because really? You’re insulting your date by saying that she has lousy taste in men. I’m not in a high-powered job or anything, but I have a college degree and my spouse does not. I also make more than he does. He occasionally pulls this crap on me, and it’s infuriating. Don’t be that guy.

    And consider this, too. She might not be looking for someone with a high-powered career to match hers. She might be looking for someone who can make her laugh, who can let her feel relaxed and like a person, not like a collection of professional competencies. She’s more than her job, just like you’re more than yours.

    1. Yes to this and everyone else who said it. Being told you’re too good to be dated? NOT GOOD. If she’s crazy for wanting to go out with you, let her figure that out on the date (terrifying, I know) AND, if she decides after that date that hey, she was right and you are an awesome person to spend time with? TRUST HER.

      Also, don’t talk about work. Not because of the “she could be your boss” thing, but because no one wants shop talk on a first date.

      1. Oh man, EXACTLY. To both of you. Women with high-powered careers have been told often enough that it intimidates men too much, so really, don’t give that impression.

        And yeah, mentioning work or figuring out if you mutually know some people through work is OK… but the subject should be changed quickly. I, um… actually have never ever dated someone in the same industry as me, because I hate talking about work on dates so very, very much.

        Plus, even if she is really conventionally attractive, there’s no reason to assume that “really conventionally attractive” is her type. Some women just enjoy guys who are stocky, or bald (jeez, just think of all the action stars who’ve shaved their heads for movies!) or look a lot more at facial structure or gorgeous eyes than “does he work out two hours a day”.

  9. Have a plan, but not A PLAN. If you are too inflexible or take too much charge, it comes off as controlling.

    Say something like; “I’ve been meaning to check out this exhibition / pub / whatever. You game?” If she hates art or beer or whatever, have a back-up location, or say “Anything new you’ve been meaning to try?”

    Avoid places which are remote or devoid of people so she is secure.
    Avoid places which are too crowded, because it’s loud and annoying and hard to talk.
    Meet in a central location, easy to get to, easy to park.
    Don’t go to a movie or seated performance first– go somewhere where you can hang out and talk. Exhibitions or museums could be fun, with coffee afterwards.

    Have fun!

  10. don’t over complicate things. she’s a nifty chick, she thinks that you’re cool. why not use that as your baseline and just enjoy spending time with a hot babe?

  11. yes! good advice!

    I think the other commenters have pretty much covered this, but I feel the need to spell it out explicitly: there are other kinds of success in life than the kinds that show up in google search results. I’m thinking of more fuzzy, but also more important kinds of success, like being a mature, interesting, happy, well-adjusted person.

    maybe (honestly, hopefully) she doesn’t really place much importance in the brand-name prep school her parents sent her to, or her brand-name college, or her brand-name workplace and job title. the fact that she reached out to you is a good sign on this front. she’s interested in people who are awesome human beings, regardless of their credentials, and you’ve come across as one in your communication with her.

    so, it’s obviously hard to push all the information you now have about her out of your head, but the one way you can “live up” to her, so to speak, is to do for her what she’s doing for you, and breeze over all the bullet points on her resume in favor of getting to know her as a real person.

    also, god, can you imagine being featured in a “most eligible singles” article in the paper, and then having anyone bring it up, ever? I’d be so embarrassed.

  12. Yeah, so everybody’s already said it but I’ll corroborate. This is going to sound like icky game/market speak but I think it’s true: the more badass a woman is, the more likely she’s OK with dating “down”. After all, there probably aren’t that many men “above” her to choose from, and those men are choosing from a much larger pool of women “below” them.

    Let me tell you my story: my partner makes less than half what I do, comes from a lower class background than I do, and at least in terms of raw computational power, isn’t as smart as I am. (emotional intelligence is another matter entirely) Which turns out to be completely irrelevant. What is relevant: we just plain WORK together. We did do the coffee date thing, except that it turned into coffee, followed by wandering around window shopping, followed by going to another coffee shop, and staying until they closed because we turned out to just have so much to talk about. That was eight years ago, we live together now and we still can’t get enough of eachother.

  13. Definitely don’t feel like being blown away by how amazing she is has to be your shameful little secret. Who doesn’t like to be told they’re amazing?

    I know, though, your real sweat is how to talk about *yourself* without feeling all pathetic. I suggest amusingly self-effacing, with a very light touch, then moving on to other subjects. Do not feel like honesty/openness mean you have to lay your inadequacies and insecurities out on the table in all their gruesomeness. We all feel squishy and insecure and inadequate on the inside, and put our very best “I’ve totally got my act together” face on for the world. Don’t compare your squishy insides with her capable, confident-seeming outsides and think it means she’s better than you, or that she thinks she’s better than you; it’s apples and oranges. No matter how confident she seems, inside she’s wondering whether you think she’s pretty, and interesting, and fun to talk to, etc. etc. (even if YOU think that’s a “duh”).

    If you are a smart, funny, personable guy as you do indeed seem to be, chances are you have other interests and priorities besides work. Whether it’s just that you have great friends you do fun things with or the traveling you’ve done or the sport you love or whatever, talk about that stuff. It’s a date, not a job interview. She wants to know she’ll have fun with you, that you’re kind, that you make her smile and want to touch and be touched… not what your resume looks like.

    Lastly, as a grad of snooty girls’ prep school, top college, and ivy league grad school myself, let me just say I am not stupid enough to believe everyone else has had the opportunities I have been lucky enough to have, or that the world really is meritocracy where if you’re awesome you’ll be at the top of your field in no time. The people I love and respect are all over the map, CV-wise. The only problem I’ve ever had was with one friend who consistently put me on a pedestal I never thought I belonged on, then made little (and occasionally not so little) digs accusing me of thinking I was better than her. By the time she admitted that it was all projecting, I had decided I was done. With clarity acquired in part by reading this blog 🙂 , I had emotionally extricated myself. SO: do not put her on a pedestal just because she was fortunate enough to go to awesome schools that opened doors for her. Date the woman not the resume.

  14. I’m not going to pretend to be brilliant and badass, but I’m definitely a “Put Together Smart Girl” these days, at least as lined up with my peers; I graduated summa cum laude, got a full-time job a few months out of college, moved out, do well for myself. My partner left college after barely any time at all, lives at home, works at a food truck (…okay, granted, they manage the entire kitchen during the night shift and are relied upon by many, but still, food service is not their life goal). I make much more than my partner does; I am somewhat better educated, although not necessarily smarter.

    We also met online. I messaged them first, but ended up being courted in the sweetest, cleverest, sneakiest way possible, and now we’re a year and a half in and about to move in together. I’m not attracted to their job or their college degree or their money–I love how we can scream with laughter while comparing crazy ex-girlfriends, on the highway late at night, how they call me Bones (from Star Trek), how we both are crazy for Doctor Who.

    It never even occurred to me that the differences were an issue! I think that is what I am trying to say to you–if this turns into love, none of this will matter the tiniest bit, to either of you.

  15. Bad Ass Chick may be an overachiever but have little else in her life, and be looking to change that. Sometimes people achieve those high goals by sacrificing weekends, friends, hobbies…and finding someone who she feels like still has his feet on the ground would be a plus. Maybe in her high-powered work world, all she meets are ladder-climbing douchebags.

    And it’s a common enough phenomenon that women in “high positions” occasionally suffer from imposter syndrome – they actually feel like they aren’t as amazing as their life position makes them seem. Insecure? Sure. Human? Totally. She may not walk in like an armored truck and demand you kneel before her. She may be so relieved by a bowling date where she doesn’t have to schmooze in a suit like she probably has to do all day at work that she will kiss you for the sheer joy of feeling like a real person.

    My resume is unimpressive; what I know about high-powered gals I know from my high-powered friends. But like the above commenters say, they all fart, put their pants on one leg at a time, kill African violets, and want to be loved and valued for who they are, not what they achieve. She likes your style – you don’t need an Awesome Castle.

  16. Do you think you’ve already idolized this girl too much? I once fell for a guy who looked GREAT on paper. Turns out it was a terrible emotional match and he had some pretty serious family and drug use issues. But on paper, wowza! My mistake was that I was overly influenced by the Idea of him and this got in the way of making an accurate assessment.

    So, remember she’s a real person and may have some major flaws. Google can’t find all the deep emotional or personality issues.

    If the conversation doesn’t flow, or if you feel insecure around her, you have to ask yourself whether it’s a good match. If those things happen, it’s not your fault. If you have anxiety issues (believe me, I understand) it’s totally important to feel at ease with your date. One idea is to focus on assessing the comfort level rather than comparing CVs.

    Good luck, but remember that there’s a ton of educated, employed girls out there to date. If it doesn’t work with her, I have a few friends who would probably love to date a fan of the Captain!

  17. My husband’s friend dated a supermodel. What does he have? I honestly don’t know, because I find him obnoxious, stunted, and hygienically suspect — but the point is, she liked him. So, what I’m trying to say is, it’s okay to be you, even if you don’t think that you is Good Enough.

    Not that I’m suggesting you’re any of those bad things, I don’t know.

  18. I think all of the previous advice is great! As a fellow “Girl with her shit together”, I totally agree that it is most important to focus on what you like about her but stay confident in who you are! There is a level of self-confidence that these girls must have to achieve such success, and nothing turns us (or at least me) off more than someone who doesn’t have the confidence to go after what they want. My husband and I struggled with this issue for many years. We were married before I went to graduate school. What finally solved our conflict was when he realized that I truly love him, and all I wanted was him to love me in return. If you decide you like this girl, know that you are also an incredible person, one way or another, and go for it!

    One thing I noticed that no one touched on is your statement: “None of this (other than her employer) has been brought up in conversation”

    There could be several reasons why it hasn’t been discussed, but I think the most likely is that she prefers to keep her successful career life separate from her dating life. She might think that telling you all of these fascinating facts will scare you away, for exactly the reasons you state in your letter. I assume she was hoping to avoid these fears. In addition, these facts contribute to her career self, but they do not make her who she is! Maybe she loves Audrey Hepburn and the Beatles, or maybe is a person who won’t watch a movie unless it has multiple explosions and gratuitous sex! You have the opportunity to get to know the real person, not just the successful, sexy woman she is. Take the opportunity! Get to know her! Give her the benefit of the doubt that she contacted you because she was interested in YOU! But most importantly, be yourself and HAVE FUN!!!!

  19. You don’t sound like the guy in this scenario, but on the other hand perhaps you might want to unpack what it means for you when you feel you are “second fiddle.”

    What would the expectation be if you were a woman and this bad-ass were a dude?

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