Dating Open Thread: What’s Your Best Dating Advice for Career-Driven Women?

dating advice for career-driven womenHappy Valentine’s Day, ladies! If you’re happily partnered, what are you up to tonight (or this weekend)? If you’re still on the hunt for a partner, though, let’s have an open thread to talk about dating. What are your favorite online services or apps? Have you joined any IRL activities to try to meet someone? Are you open to dating at the office (and how does that look in 2018)? Whether you’re partnered or not, what is the best dating advice for career-driven women you’ve ever heard?best dating advice for career-driven women - image of heart marshmallow in cocoa

For my $.02, I’ve said it before, I’ll say it again: I’ve always been of the view that I’d rather be alone than with the wrong person — and knew it was time to break it off with guys as soon as I rolled my eyes at them. As a Type-A, career-driven woman, the best dating advice I got back in the day was to treat dating like a project, with measurable goals (update profiles on 2 sites this week, message 4 prospective guys, go on 2 dates). It gives you some feeling of control over what is essentially an uncontrollable process — and it helps you understand better what you do and don’t want, as well as appreciate when there is a spark or connection. Personally, this last part was really important for me — I went into dating like I might a hire, with a wish list of schools, careers, extracurriculars. Looking back, I’m glad I ditched the list and focused instead on spark, connection, and shared values and expectations about what our lives would look like, including things like how much you want your extended family in your life, what the “default weekend” looks like (together? apart? partying? with our kids? football widow?), and even generally being on the same wavelength on things like dirty dishes and toys taking over your living room. That said, I wound up meeting my husband at a friend’s party a few months after I’d decided to take a break from dating like a project… and both of us nearly hadn’t gone to the party. So luck (obviously) plays a huge role… but as the quote goes, chance favors the prepared mind.

Here are some of our previous discussions on point regarding dating advice for career-driven women:dating advice for career driven women - image of pink heart in hot cocoa mug

We rounded up our best dating advice for career-driven women -- including how to treat dating like a project, how to ditch the list, and what's really important.


  1. This is timely for me because I’m throwing myself into online dating right now. I figure it’s now or never. It’s never been successful before and I don’t have high hopes this time but I’m trying. This time if it doesn’t work I will hang up my spinster shingle because in the immortal words of Charlotte from SATC, “I’ve been dating since I was 15, where is he?!”

    I find it so hard to even match with somebody let alone get a date. I swipe and like and message and it mostly comes to nothing. Or I only get messages from gross weirdos.. I’ve already really lowered my standards. Normally I would shy away from divorced single fathers but I’m not counting anyone out this time. And still it sucks and it’s hard and feels so pointless.

    Sorry about the rant…I think all the Valentine’s crap on instagram has struck a nerve.

    • Your post is exactly what I was going to write. So much this. I’m not interested in the guys who are interested in me, and the ones I’m interested in aren’t interested in me. I’m 32 and some days I feel like I should just embrace the reality that I’m likely to be permanently single.

      • I’m 32 too, almost 33. I know all the married women will now chime in with “But 32 is so young!!!” It is young in some ways, but not when it comes to dating.

        Kat, maybe next year for Valetine’s you could do a post about embracing singlehood or loving yourself without a man….instead of a post about dating.

        • Anonymous :

          I’m single and 34 and think it’s young to be concluding you’ll never find someone!

      • Anonymous :

        I just read in the NYT yesterday about how in happiness studies of married people and single people, the slight difference in happiness levels between the two (single people are slightly lower) may actually be attributable to the small subcategory of single people who just left relationships and are still processing the break up. Otherwise, single people (on average) may be equally happy or happier than married people!

        • To the anon posting about the NYT article–I’m not sure if you’re single or married; I will tell you that this is not super helpful for those of us who long to be in relationships. We read all these studies, we know all the self-help advice, we know we might not be happier in a relationship, but it is excruciating to be told these things over and over again when we’ve been looking for a partner for a long time. So…I know this was very well intentioned and that it wasn’t mean or anything, but it doesn’t feel kind or helpful, either (even if that’s how it was intended). Just food for thought for when you (or anyone) talks to a friend who has been single for a long time and doesn’t want to be–we don’t want to hear these things.

        • Anonymous :

          Well, seeing as how I’ve experienced myself in both single and couple states, I can definitively tell you that I’m happier, on balance, in a relationship. I can also say that even the moments of unhappiness in a good relationship don’t outweigh the great ones. I can definitively say that even though I’m generally happy when single, I still crave certain things about being coupled.

          So all the studies in the world that talk about how people feel on balance are useless compared to my experiences… which are as close as you can get to a controlled study.

          I know you meant well, but this does not help. What am I supposed to feel? Oh, great. Statistically, coupled people aren’t happier. All the sudden my longing for love and connection has vanished. No.

      • Me too. As a career attorney at law in NYC, it is impossible to find a guy that I want that wants me for more then 1 nite in bed. The decent men are already married, or gay, or to old for me. I do not want a guy over 55, but many of them that old are divorced with kid’s my age! I do NOT want to date a guy who will be wearing Depends when I want to go out to eat! FOOEY!

        Guys my age are to immature, and Dad says many of the decent ones are playing the field, knowing they can bed a different girl every night and get away with it. I want no part of any of that, b/c Dad says when you have s-x with someone, you are having s-x with everyone they have EVER had s-x with! DOUBEL FOOEY! I do not want to have s-x with all of those other people! TRIPEL FOOEY!

        I suggest the members of the HIVE who know decent guy’s put them into touch with women like me. At worst, they won’t be any more of a looser then the schmoes I’ve dated (and who wanted to mate with me). If they are any good, I will at least have a shot at getting MARRIED to one of them and retiring from all of this work! If I do, I can truly say YAY!!!!!!!

    • Don’t shy away from divorced dads (unless of course you don’t want to be involved in raising children) – one of the nicest guys I know is a divorced father. I would set him up with a single girlfriend without hesitation if I had any close friends nearby who were single.

      • It’s not the kids that scare me, it’s the ex.

        • Anonymous :

          This, so much. I’ve very recently gotten involved with someone with a child, and the ex has made it a point to try to make my life difficult. The guy is great, but I’m not sure that even a wonderful guy is worth dealing with this drama.

      • ManagementConsultant :

        I’m 32 and single, and my concern with divorced dads is that it’s a very different lifestyle than what I want right now. I do want kids eventually, and am well aware that time is running out for me to do so biologically. But I don’t want the pressures / time constraints of children and shared custody when I am trying to get to know someone for the first time. Does that make me unreasonably picky? Maybe, but I’m sticking with it. I don’t completely rule out divorced dads, but it’s a demographic I prefer not to date with all else being equal.

        • Anonymous :

          Same. I don’t think I want kids, so there’s that, although I understand that step kids is different than having your own. Kids are just such a huge part of someone’s world… and they will feature in the relationship. Also, I want to be someone’s priority–I’m 30, never married, and I want to experience that. Dad should be prioritizing kids.

    • Anonymous :


      I’ve been single for the better part of the last 5 years. I just had another potential relationship dissolve and frankly I’m done. Hanging up the shingle. I give up. I truly do not believe there’s a person for me out there.

  2. Anonymous :

    I’ve spent about 5 years single, honestly struggling to find anyone online who even wants to go on a date with me! I’m seeing someone now who I met at a friends party. I suppose the take away is Go To Things! Be Open! But actually I think that is nonsense. It’s all down to luck

    • I love that I’m supposed to put myself out there and go to meet ups and aggressively date because it’s a numbers game, but also “it’ll happen when you least expect it!” and I’m supposed to be 100% happy with my life without a man.

      Sigh. Definitely not trying to contradict your post in any way– just expressing exasperation with the whole thing. It is luck. And timing.

      • Anonymous :

        Yup. I hate it all too. I just got lucky eventually for no apparent reason, and for all I know it will be over in a week.

      • smugmarried :

        I hate the “it’ll happen when you least expect it” theory with a fiery passion and blame it for at least 5 years of my own singleness. Time and effort (and lots of luck) help with every goal in life! I can’t believe I feel for the line that dating was the one exception.

  3. Anonymous :

    Five years ago, I set up an online dating account at the advice of my counselor. I was in the process of healing from a major life crisis and a rough breakup the previous year. Until then, I’d been firmly against the idea of online dating, and I also didn’t think I was ready to start seeing people, but my counselor encouraged me to give it a try, with no expectations except to improve my social skills and have fun getting to know people. (Also, I lived in a small college town at the time and had few opportunities for meeting anyone.) I went on four first dates with four great guys, and ended up marrying one of them.

    I agree with Anon at 1:09, a lot of it comes down to luck, but there’s definitely something to be said for being open to new experiences. You never know what will come of it.

    • Yes, but… like, how open? I’ve done a lot of online dating now, and I haven’t married any of them yet.

      • Anonymous :

        +1. And…there’s a reason a lot of those guys in my age range are still single (or single again). If you haven’t tried, you should definitely try online dating…but it’s not the missing link.

      • Anonymous :

        Yup. This kind of advice (“be open to new experiences!”) is useless to single people.

        • I’m not saying that being open to new experiences is a panacea. All I’m saying is that at particular point in my life, it wasn’t useless to me.

        • smugmarried :

          This advice was useful to me at some point in my early 30s. I can only speak to my own experience but I had a very narrow idea of the person I wanted to be with and I really needed to expand it in order to find someone. There is a “This American Life” episode where they do the Drake Equation for dating. In my case it was something like #men in my city * % never married * % with education desired * other qualification = N. N turned out to be such a small number that it was clear I was being ridiculously picky.

      • Anonymous :

        Also, online dating has changed a lot over the past decade and especially over the past few years. I used to use OKC with decent success- nice place to find quirky, smart guys and actually engage in conversations before meeting. Now its just an endless hinterland of swiping and matching on apps and either no communication or BS small talk.

        • Anonymous :

          I just signed up for OKC again recently and I was really surprised by the changes. It’s more like an app now. I swipe and swipe and zilch. I used to get lots of messages from guys on there.

        • +1 – I’m not sure it works as well as it used to.

  4. Anonymous :

    For me in retrospect, I met the best guys in grad school / professional school. But I wasn’t ready for them then, and I’m not sure they were ready for me!. Since then, I have met the best guys through those school connections/ friends of friends. But no matches. So I’ve chosen life/career/friends/family over men. And I’m happy with that now.

    Interestingly, my friends on their second marriages all matched up quickly using various online dating sites / Apps. In my age group (now 40’s) of women marrying for their first time, all successes were with men much older (eg. 10 years), divorced, with kids. It’s a lot of sacrifice to marry in that scenario, to me, and knowing that you will be a widow or possible long term caregiver much younger (if you are lucky). It is what it is.

    • Anonymous :

      Eh, I don’t know about that last part. My best friend married a guy 10 years older than her and he is in amazing shape, healthier than all of us, and is very proactive at managing his health. I have another friend who just lost her husband – he was 46, she is 45 – to a heart attack because he wasn’t taking care of his health. None of us ever knows what’s going to happen in the future, but with someone who is healthy and health-conscious, I think the odds are okay.

  5. I love that I’m supposed to put myself out there and go to meet ups and aggressively date because it’s a numbers game, but also “it’ll happen when you least expect it!” and I’m supposed to be 100% happy with my life without a man.

    Sigh. Definitely not trying to contradict your post in any way– just expressing exasperation with the whole thing. It is luck. And timing.

    • Anonymous :

      Amen. It is so conflicting and confusing.

    • Don’t forget that you’re supposed to fill your life with fun, family, friends, activities and hobbies in order to have a full life and seem interesting to a man. However, you’re later supposed to drop something to make time for him.

      • Anonymous :

        And at the same time you should never drop anything to make time for him because then you’re “too available” sigh.

  6. Two things that (eventually) worked for me:

    1. Reading Evan Marc Katz’s work (a quick web search will turn up his stuff) – I don’t buy all of it, and it took about 8 years for me to really internalize the part about not investing until a relationship is real, but I finally got there.

    2. Treating dating like looking for a job. I assumed that it would take 12 in-person dates to meet someone I liked who liked me back during each post-breakup round of dating, and when a date went badly or a guy didn’t call, I checked his name off and moved on. In my last round of dating, I dated Guy #1 for a couple of months, and when that didn’t work out, figured I had to get to 24 before I met another with mutual liking. My fiancé was #23 of 24.

    • Baconpancakes :

      Oh man, actually yes to #1, now that you mention it. I had completely forgotten. I don’t buy into Evan Marc Katz’s full philosophy, but following the whole mirroring thing – where I wouldn’t text or call more than he did, and I would continue to consider other people for dates until we had an exclusivity talk – probably helped. My SO was previously pretty gun shy, and before me had dated a couple of women who were very intense and demanding about relationships, but the attitude of “don’t invest until there’s something to invest in” absolutely helped my mindset.

      • Pretty Primadonna :

        This, this, this!

      • Senior Attorney :

        I have never heard of this guy, but my rules were absolutely “I don’t chase boys” and “I don’t date anybody who isn’t excited to be dating me.”

      • Anonymous :

        The whole “it’s not a relationship until you both think it is” thing is so critical. Absolutely do not stop dating other people until there’s a mutual decision to lock things down. Men don’t stop dating other women until there is an explicit discussion about stopping; women will stop dating other guys after two dates with the same guy, before there’s even a hint of a conversation about a relationship. It’s giving loyalty to someone who hasn’t earned it and may not deserve it, and in the meantime, you may miss out on someone who is interested in earning your loyalty. And while some people consider this “game-playing,” IMO it’s never a bad idea for a guy to know that you have a life – and other options – and aren’t sitting by the phone waiting for his text.

  7. What is the point of that stupid, floating bar at the top of the screen if you can’t even get to the home page from it?? I guarantee you I’m never going to click on the About or Contact pages.

  8. Baconpancakes :

    My last two relationships, one of which seems to have stuck, came out of periods when I was dating casually online and just enjoying my non-dating free time with friends. Both times, one of those friends, whom I hadn’t thought of as a potential partner, stood out as someone I really wanted to spend time with, and eventually I realized that I’d rather date them than the dudes from online dating. Not everyone is going to have a friend like that – but I think there was something about feeling like I was doing everything I could – ie online dating like crazy – that let me relax enough to be able to actually see what I wanted.

  9. I will plug Hinge for a dating app. I met my husband through it but what I really liked about it is that it connects you to friends of your facebook friends, so there’s a degree of familiarity that made me more comfortable in the online world as compared to complete strangers. DH and I went to law school together but for various reasons never met each other – and now I can’t imagine my life without him. Hinge helps you find folks you should have met the first time around but for some reason didn’t!

  10. For what it’s worth….I used ALL the dating sites at some point in time over my 20 year dating history. And I HATED when people told me “it would happen when the time was right” or to “just be open.”

    At the age of 37, I went online for one more chance to find someone special (and still have at least a shot to have a family).

    I was on the absolute WORST date of my life (and I have had some really awful dates) and my date was in the bathroom (thank God, because I so needed a break from him). In an attempt to find someone (ANYONE) that could give me hope, I broke one of my own dating rules and opened up my dating app while he was away from the table. As it happens, I had received a message from a man who didn’t meet all of my “requirements” from a profile perspective but I grabbed onto his message like a lifeline.

    I fell in love with that man who messaged me and married him last year. I would have overlooked him because he was married before and wasn’t sure if he wanted children (which I definitely did).

    It turned out that he wanted to have children with the right person and I could have closed the door on my soulmate and best friend because of what his profile said. I always wonder if I would have passed on him if I hadn’t been on my worst date.

  11. Anonymous :

    So the post’s question was “what is the best dating advice for career-driven women you’ve ever heard?”

    For me, the best advice was to let go of ‘planning’ who was right for me. You can’t plan love like you can plan a career. I’m pretty type A and assumed Mr. Right was taller than me, dark hair/complexion and loved dogs. Actual DH turned out to be same height/borderline shorter, blonde, hates dogs. Totally would have swiped right past him in online dating without that advice.

    Second best advice was to be honest about how important your career is to you. I told DH right from the beginning that I would not assume that my career played second fiddle to his. He was onboard with being an involved dad and a two-career household.

  12. My quick reaction to this question is: don’t! But I know that some people really want to find a partner, so my answer is not helpful.

    I am similar to another poster in that I have given up dating seriously. The man who is my current $ex partner is someone who I connected with on IG. I suggested meeting up, then after flirting for a bit, I said here’s my deal – I don’t want a relationship because my life is full of things that I love and I don’t want to give any of that up, but I like having a regular $ex partner so why don’t we get together and see if that clicks. It did and it’s quite enjoyable. He’s a good dude, there is zero pressure because neither of us have any what are we questions or down the road questions, we are both very honest with each other about what our needs and wants are, and if one of us decides to go a different way, it’s NBD. He is someone I would stay friends with and he feels the same way. Did I find a life partner? No, but I also am not interested in compromising my life right now to fit a life partner in, so it works.

    • *Note: I gave up after having one guy who represented he wanted a serious relationship but when presented with what I needed in one said he couldn’t give it to me (met on Bumble – nice guy, still adore him but oh well). One who was emotionally abusive (we knew each other from college) and another who was borderline emotionally abusive with serious emotional baggage (set up by friends).

      HARD PASS on dating.

  13. Pretty Primadonna :

    My advice might be seen as pretty aggressive, but I was serious about finding love and getting married.

    (1) Enjoy the life you have now. There is no sense in wasting precious time being sad because you are single (ask me how I know…)

    (1)(a) If you haven’t already, accept that life may happen a lot differently than what you envisioned or planned. Be okay with different and maybe even (usually?) better than what you imagined!

    (2) I might catch flack for this: when you go out, make it a point to look put together and approachable and friendly.

    (3) If you see someone you might be interested in, smile and greet them. If they’re interested back, 9/10 they will strike up a conversation. If “hello” or “hi” doesn’t work, offer a compliment. Show that you are open to being approached by them.

    (4) If you are out with a group of women and see someone you like, try to break away and make eye contact. Perhaps even smile and speak. Most people are not going to walk up to a group of women and try to holla.

    (5) Go to events where the folks you’re interested in are. Gun shows. Engineering conferences. Skateboard park. Wherever.

    (6) Know what your dealbreakers are. If someone you are dating exhibits them, cut it off and move on.

    (7) Make dating a priority.

    May the odds be ever in your favor!

    • Senior Attorney :

      I think this is all good advice. And I’d add what I posted above: Don’t chase after people who are not displaying a good amount of interest. People who want to be with you will make it happen. If they’re not making it happen, they’re just not that into you.

  14. Happily partnered and playing Pandemic Season 2 tonight. Boy howdy, season 2 is harder than season 1!

    My dating advice, for whatever it’s worth, is, don’t settle. For years I met and dated people I knew weren’t right for me, but I didn’t listen to my instincts about them because I felt for some reason that it was incumbent upon me to “give them a chance” and then keep giving them chances for ages after they proved they didn’t deserve them (or maybe after we both proved we weren’t compatible, to me slightly more charitable/accurate). Then I met someone I clicked with through Coffee Meets Bagel, and, wouldn’t you know it, years later he’s still on chance one, because he just is awesome and he doesn’t need more chances.

  15. Matchmaking :

    Has anyone tried matchmaking or “It’s Just Lunch”? Every time my mom pesters me about not dating (and not having a lot of success with online dating), she suggests one of those paid options. I’m guessing they’re scams, but would love to know first hand!

    • I’ve posted on this before, but my husband used to get matchmakers contacting him through dating apps to be one of their “men” (i.e., he didn’t pay the service, the women did). He tried it out and said the matchmaker was a lot less thoughtful about the match than he would have been (i.e. “She’s looking for a professional guy, he’s a professional guy, go!”). His takeaway was don’t bother, do your own picking – you probably know more about what you want. I have a few friends who’ve tried them too with no success, but who found partners through dating apps.

      • Matchmaking :

        That’s what I thought, I kinda figured they were scams. But interesting to know that there’s a shortage of men and the women pay for it! I would have thought it the other way around…

  16. I got divorced last year and was not really ready to date. Until I found out, halfway through the divorce that soon-to-be-ex had multiple affairs during the time of our marriage. I was divorcing him for other reasons. You all may remember me I asked about us divorcing without a lawyer (I am one) and we sort of ended up just agreeing to details and having a lawyer draft it up. I got the kids full time and couldn’t see myself having time to date until they left the house. But I wasn’t particularly good at dating the first time around and I thought I would need practice so that I would be better at it in 5 years when my kids left home (I am a planner) so I signed up for Match and eHarmony. Also something about the betrayal made me want to test my desirability. eHarmony matched me with people way too far away and many of them seemed inactive, I never even communicated with any of those people. Match gave me a TON of matches but most wholly unacceptable. Then I got sick and had time to be on Match and I began communicating with several men (maybe 10 over a two week period) and most of them after a couple emails I didn’t want to meet. But I went on one in person date. And I liked him. So we went on another date. And another. And now it’s been six months and I’m crazy about him. I did sign up for a year of Match but I haven’t had to go back on it because I am smitten. In some ways we are a lot alike — divorced parents of teens, sporty, non drinking, go to bed early, similar values. In other ways we are not — he went to community college and works in a blue collar job, although he makes good money. But at this stage of the game that status stuff matters less to me — he is smart and funny and kind and cute. The logistics are complicated because I have my kids full time and I work a lot — remember, I wasn’t planning on doing this for 5 more years. But it’s super fun and I am light and happy and joyful in a way that I haven’t been — well maybe ever. So here’s one vote for on line dating.

  17. AuntieCam :

    Thanks to all. Was feeling a bit bummed with the lead up to the day, it probably doesn’t help that I just came off a kinda intense 2 week trip abroad (religious pilgrimage) and am sorting out the feelings on that, including traveling in a group (NOT recommended.) In looking at my life of dating, I have concluded that I do better going out and talking to guys that intrigue me, than online. Definitely plan on looking up some some of this Katz stuff because I may need that in my arsenal as well.
    :) Thanks ladies!!

    • Oh no! I’m sorry to hear your trip didn’t go well. I don’t know if you only do religious travel, but I actually just got back from a group trip (non-religious, just regular travel) with total strangers that I absolutely adored–it was through a company that is focused specifically on 30s and 40s solo travelers. It’s one of the best things I’ve done recently. I’m happy to chat more about it if that sounds like something that might help make future travel happier (but obviously if you’ve sworn off the group dynamic, feel free to ignore!).

      • AuntieCam :

        Thanks! I only did this group because it was religious and there was some appeal to having people who were focused on that part and having a religous at the ready. But I was just in a different mindset from many people given a background of working in international aid, etc. I think group travel works for some cases, not sure it was the right choice here:). Appreciate the offer and glad you had a great trip!

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