A Guy’s Advice For Women – How to Turn a First Date Into a Relationship

Woman and Man

All of the rules are irrelevant: either you are getting along or you are not getting along.


Note: once again, I’m inspired to write a (male heteronormative) response to a list from IDatedThatDouche.com called 10 Points of Advice to Men When on a First Date With a Girl.

  1. Dress Like You Give a Shit – This may sound obvious, but you would be surprised how many dates I’ve gone on with women who threw on the most casual outfit imaginable, were all sweaty from biking, and acted like they could care less. I mean, fair enough…maybe they weren’t into it. But why show up in the first place then? I’m not saying you need to wear an evening gown, but if you know you are going to a nice restaurant, dress for the occasion.
  2. Don’t Have Sex – Ok, here is the reality: some (but definitely not all) men are looking to get laid as soon as possible. If we sleep together after the first or second date then we may get the message that this was a one-night stand, and split. The caveat here is if the guy really likes you, sleeping with him on the first night probably won’t make a difference; he will still want a relationship (also if you have been friends for a long time, then this isn’t really a ‘first date’). To hedge your bets, it’s probably best to be flirtatious and make it clear that you are interested in a romantic relationship, but to hold off on sex until the both of you are interested in something stronger. You will lose some douchebags on the way and will avoid a lot of mistakes.
  3. Turn Off Your Phone – Honestly. Show some respect and stop texting/Facebooking long enough to have a conversation. You can ‘like’ Melanie’s Cabo vacation photos when you get home.
  4. Relate – I have gone on enough dates to learn that the success or failure of a first date is a witches’ brew of attraction and good conversational flow. It doesn’t matter what you talk about; it matters how you are relating. All of the rules (don’t talk about exes, don’t brag, listen more than talk, etc.) are irrelevant: either you are getting along or you are not getting along. If you are both having a riot of a time making fun of your exes, go nuts. If you both enjoying the silence, or joking and talking over each other, enjoy it. If you don’t relate, it doesn’t matter anyway; just move on.
  5. Relax – Relax. Have fun. The less you stress the better it will go. If you both want to go get hammered at a bar, go nuts. If you just want a glass of wine, treat yo’self. Just don’t be so stressed out or uptight that all of your walls are up and you are on the defensive. Yes, your ex was horrible, and you had this crappy one-night stand with this guy you liked and he didn’t call…I get it. Trust me, I’ve been there too. Men have just as many insecurities. Being cautious doesn’t mean shutting yourself off because of your past. Learn from your mistakes, but don’t be afraid to have fun, be honest, and be vulnerable again with somebody new.
  6. Money Isn’t Everything – It isn’t. Really. Stability is far more important. Surface level wealth is deceptive. If a man drives a BMW and wears an Armani suit, it may mean he is eyeball deep in debt. It may also mean he makes impulse purchases for himself before he thinks about his future or other people. Drive around a wealthy neighbourhood; you will see a lot of older men and women wearing relatively frumpy clothes with modest sedans. Read “The Automatic Millionaire“. I’ve often been in an unstable place in my life (moving to a new city, in flux with work, casually dating), and when I have been in that place, I was not interested in a relationship.
  7. Don’t Judge Him For Having Too Many/Too Few Sexual Partners – This goes both ways, of course. I think it is smart that both of you get tested and use protection, particularly in the early stages of a relationship. That being said, when people are single, they sometimes sleep around, and over a few years that can add up. This doesn’t mean they are incapable of having a relationship. Then again, sometimes you just don’t really meet anybody until later in life, and that’s fine too. Some of the best, coolest people I know lost their virginity late in life. They spent their early years becoming really, really awesome. 
  8. A First Date Isn’t Everything – Oh, you ‘caught a friend vibe’ the first date, so that’s it? You are moving on? You may have missed out on something great. A lot of solid guys aren’t sexually aggressive on the first date, because of all the years of being told that we should be gentlemen. No, we are not grinding our dicks on you in a nightclub. We want to, you know, get to know you first. Ok maybe it’s just that, in North America particularly, a lot of young men don’t have the vocabulary we need to express sexual interest in the way that is 100% smooth. Either you have guys who are way too forward, or you have guys who seem almost asexual. I guess what I’m saying is, you may want to account for this general confusion…
  9. Be Honest From The Start – If it isn’t working, fair enough. Just keep it real. It might hurt, but it’s better than being strung along. At the same time, be honest with yourself; are you cutting yourself off because of your past? What is it you really want in a partner? Be honest about where you are in your life, but understand that if you are really depressed and really sad, it might be a tough sell. Be honest about what you like and who you are. You might be surprised! That thug might be really into classical music; That nerd might love hip-hop.
  10. No Tests – I hate tests. Tests are a great way to piss somebody off and accomplish nothing. Don’t test your boyfriend. Don’t try to trick them into fucking up. If you want to know something, ask. You test too much, and you might just get the result you were looking for.

Image of woman and man on a bench courtesy of Shutterstock

About Josh Bowman

Josh Bowman is a professional fundraiser, story-teller, comedian, and blogger. He has worked and consulted in Vancouver, New York, and now Toronto for almost a decade. Josh improvises around Toronto, including regular shows with Opening Night Theatre, and also blogs for the Huffington Post. You can email Josh here.. If you want to know more about Josh, check this post and this post out first.


  1. Women will always test. It’s part of evolution. It’s her way of screening a possible mate. A way of qualifying him. And it can be conscious or subconscious. She shouldn’t be mean about it, though.’

    Asking a woman not to test is like asking a man not to be interested in sex. We’re all just wired that way.

    • elizabeth english says:

      Speak for yourself Claire.

      I liked this article BTW.

      • That’s good for you. I refused to date for many years because I didn’t like the way that women were treating me and I couldn’t figure out how to find the ones that were going to treat me well that hadn’t already been snatched up by some lucky guy.

        Women that have standards for themselves will always have men available to them. It’s mainly an issue of figuring out where they are and the willingness to date friends. It might require being willing to SIU and make the first move. But, here in Seattle there’s a ton of amazing guys going without dates that are only available to women with standards that are willing to go out and get them.

        Eventually, I figured out that online dating solves a lot of that, as I can prescreen for at least some of these things. I’m not going to refuse to date a woman that’s willing to have sex on a first date. However, for me, I’ve been treated like a sex object by enough women, that I outright won’t have sex with anybody until I know that they respect me.

  2. Madeira says:

    I always fucked on the first date if I liked them, to test to see if they were a shitty misogynist who thought that me being “easy” was a liability.

    My husband likes me just the way I am, sluttiness and all.

    • Amen sista.

      I cannot believe that in a progressive men’s site we’d see the old chestnut that the woman had better not “be easy” because it’s her responsibility to make sure the guy doesn’t “get the wrong idea.” Yes, by all means let’s go back to the bad old days.

      • The writer never said that women that give it up on the first date are easy. That’s something that you’re asserting. The writer merely is reflecting the fact that a large portion of the male population won’t have a relationship with somebody they’ve had sex with, unless they’ve already had one before the sex.

        Women have a choice about when they consent to sex. If they choose to have sex with somebody before they know them, they’re choosing to deal with the consequences.

        Personally, I don’t respect people that judge men for having standards. The standards might not reflect your standards, but men are just as entitled as women to have standards about what we want in a relationship.

    • The whole idea of sluttiness is BS. There’s no appreciable difference between men and women with regards to sex drive as far as I’ve been able to tell. Men are just much more likely to own up to being sex driven than women are. At least when other men are around.

      It’s a double standard, but one that women need to address themselves first as a lot of the pressure isn’t coming from men. If you don’t like it, talk to your friends about it and end the practice. This isn’t something that men can or should fix for you folks.

      As far as sleeping with somebody on a first date a test goes. If I found out that a woman had done that to me, the relationship would be over. I treat women well and I refuse to accept this sort of bad behavior. I don’t care how hot the sex was or how amazing she was in other areas, she would be dumped immediately. Men deserve better treatment than that.

      If you want sex on the first date that’s your prerogative, but having sex on a first date as a trap is BS that I refuse to put up with. I don’t care how amazing she might be in other areas, I won’t tolerate that kind of treatment. Makes me wonder what other manipulative and emotionally abusive behaviors and practices she has.

  3. This is pretty good. There were a few here that really it home. Turn off your phone is a big one. Being a single dad, my rule is that unless it is my kids calling, I don’t touch my phone when I am on a date. I am OK with her answering from her kids as well but I have ended a date where the woman was on Facebook while we were having a drink.

    The other is number 8 and I would love to get a woman’s opinion. I had a date once and it went really well. She even said it was the best date she had ever been on. We talked, got along really well and laughed quite a bit. That said, she later told me that she didn’t want to see me again because there was no attraction. I asked her if she found me attractive. She said she thought that I was very good looking but that she didn’t feel any attraction. She then asked what was the difference.

    I explained that you can walk down the street and see someone and you think they are attractive, but to me, attraction is something different. I feel that thinking someone is attractive is kind of an instinct, where attraction can be built. You date, you get to know someone and you gain attraction to them over time. To me this is more long lasting than having one date and putting all the chips on to this one occasion. This is my opinion so I am curious what you all think about this.

    My thought is that if you don’t find someone attractive, you probably won’t develop an attraction to them no matter how long you date. However, if you think someone is attractive, i.e. good looking, it may take a few dates to build an attraction.

    Any thoughts or am I just out to lunch???

    • Neal
      “”””” get to know someone and you gain attraction to them over time. To me this is more long lasting than having one date and putting all the chips on to this one occasion.”””””””
      As long as men and women continue to use the traditional dating as their preferd way to find a partner this attraction we can feel that grows over time are not allowed to happen,
      That is why it can be better not to date but get to know a person without dating.

      For a woman to go on a second,third ,fourth date with a man that is attracted to her romantically , while she feels no sexual( romantic) attraction, that is difficult. It is a bit embarrassing. A woman can be afraid to hurt his feelings by giving hope because after all she goes out with him again and again. And if she feels his sexual tension , but are not sexually attracted to the man, then that can be aqward .

      Maybe men can go on multiple dates with women they are not attracted to in the hope they will develop feelings for her over time because she is a good decent human being. I am not so sure if men do that often.
      What do you think?

  4. This applies to both genders; I like it and please men pay attention to number 1. You don’t need to wear a suit for a coffee date, but please make sure what you wear is clean. I’ve being on a few dates where men looked like they were working on their cars.

    I have never slept with someone on a first date, but had been fooled and slept with someone after three dates. He acted like he wanted a relationship; then later said he wasn’t ready for that and just wanted a FWB. So pay attention, people are good at mirroring and pretending that they are what you want to get what they want.

  5. Ah, the timeless “numbers” issue! One thing I’ll probably be never able to get, is why do people actually want to know those numbers?It just doesn’t make sense – say, you meet someone with whom all goes well, you’re compatible, etc. etc., BUT…their number is higher than the number you deem as acceptable. And what? Will you start liking that person less just cause of that?
    I say, its not the number that matters, but the story behind it. Its totally different when someone had lots of partners because of their inability to form a solid relationship/comittment issues, etc., and when the numbers got higher because of being single for a long time. Having very few partners doesn’t really confirm the persons potential in a relationship (as it may also be because of poor social skills).

    • Hi Laura

      I wonder why Americans have this rude, inpolite tradition of asking strangers, their date for their number .

      Do they also ask all sort of other highly personal private questions to persons they are not in intimate relationship with.?
      Do you ask if they have ever had STD, the income , do they own property , all sorts of diagnoses ,
      Criminal record, .
      Do they ask for ID so they can look up the person online to do a background check ?.

      • Mr Supertypo says:

        I also wonder why, I never came across it in Europe (Italy, Germany and Scandinavia in general) but I see it a lot in American dating contest (can speak about UK or Holland, only been there as tourist, no dating) usually if it has to be asked its something you keep till 3 or 4 date. People are less likely to be honest with “embarrassing” (depends who you are, somebody may even brag) things at the first date. And IMO its also impolite to ask….but thats me.

  6. The first date isn’t everything is so true. Before meeting the amazing fella I share life with now, I dated a lot. I or the other person is trying so hard to impress someone you are rarely yourself the first date, little nervous, a little off from being that hilarious person you normally are. I always would do a 2nd date unless there was a million red flags during the first if it was offered/suggested/asked or if I felt that another time of getting to know them would produce a better outcome.

  7. This is good stuff. Too bad that most women won’t read it, and many of those who do won’t take it seriously.

    • Because it reads like satire! It’s nonsense! It’s paternalistic and condescending.

      • Can you give any specifics about what you find to be ‘nonsense’?

        • 1) The author is telling women that in order for someone to want to be in a relationship with them, they should dress up. The idea that women have to dress a certain way (“nice” and not “casual”) to make themselves appealing to men is vile. And if it’s true for the author, he mightn’t want to go advertising the fact that he’s that shallow, or expects women to dress in a specific manner just to please him.
          2) The author is explicitly telling women what to do with their bodies–“Don’t have sex”. That’s not his call.
          3) And his point that “if the guy really likes you, sleeping with him on the first night probably won’t make a difference; he will still want a relationship” can very easily be countered by the argument that if a guy i’m into would think less of me if i DID have sex with him on the first date, he’s not the kind of guy i’d want to carry on dating. That’s something i’d like to know, and there’s only one way to find out that out.

          • To be fair, the list is a response to a list of advice for men, made mostly of fail (http://www.idatedthatdouche.com/2012/08/ten-points-of-advice-to-men-when-first.html), so there’s a reasonable chance it’s meant at least tongue-in-cheek. The original list includes such classics as insisting the man pays for the first date; we’re safely in gender stereotype land here.

            But then, the original list gives advice for men “dating girls”; Why would a man do that in the first place?

            • Emma – I have to disagree with you. If women are showing up to dates fresh off their bike in yoga wear (which is only appriopiate for a bike date, dog park date or the likes of that), I can understand being a little like, “umm okay.” I wouldn’t like it if a guy showed up dressed up with what he wore to his construction job.

              I also don’t think the author was teling women what to do with their bodies so much and just being honest about how men deal with the whole thing of sex. I am not saying it’s fair. There is clearly still a double standard. But it is how a lot of guys think and the author being honest about that doesn’t equate to him telling women what to do with their bodies. He is simply saying, “ladies if you do x, men will do/think why.” While I would like things to be different, you got to work with how things are and use it to your best advantage. Hence, not giving physical affection so quickly and easily.

              • In another article on this site, men were adamant in their comments about how a girl who made them wait for sex was using and exhausting them. That it wouldn’t fly with them and that she . Now, we’re being told to wait. Why can’t it just happen organically? Neither party should pressure the other and neither should be making it into a game or ‘withholding’ on purpose. It should happen when both partners want it–when they feel comfortable and ready. Every situation is different and varies based on many different things. It could happen on the first date, or it could happen after six months. I guess I wouldn’t want a man who would judge me for either–nor would I ever judge a man for engaging in either, as long as he was respectful, communicative, and honest throughout.

                • Aya – I agree with you. I think part of what you’re saying is we should be individuals and tune in to our own rules, and that’s something I’m strongly in favor of. In this case the “rules” given are marked as heteronormative by the author but I think class is evident in his writing, so the audience is limited in that way too (full disclosure: in the past I would probably have been an ideal audience for this type of article).

                  I’m probably somewhere in between Emma and Erin in my response to the article. But part of the reason I lean more towards what Emma is saying is that I don’t see most of the things on the list as being values, and am wary of anyone who would.

              • Completely agree with Erin on this (for the record I am a smart, well-read feminist with a lot of dating/relationship experience – not that that matters, just putting my opinion in context).

          • I definitely think women should look presentable on dates. I don’t find the advice offensive at all.

            I am pro-90 rule. I would have saved myself so much trouble by waiting and just letting all the assholes LEAVE. I also think if a woman has sex on the first date, she should be cool with it just being a one night stand and not expect more.

          • Michael Rowe says:

            Uh, Emma? The author is telling women to dress up for a first date. Did you happen to catch the “date” part of that? That’s not “paternalistic,” it’s good manners. Remember good manners? Never mind…you probably don’t.

            • Michael, is it good manners to sarcastically ask someone if they remember good manners and then immediately reply “neverm ind..you probably don’t?

      • i second that!

      • Mr Supertypo says:

        to be fair its the same feeling that lot of guys get from reading dating advices to men from women and not only from women see doc. Nerdlove, who is almost always cheered (incredible but true) by women.

  8. Super advice. I’m not just saying that because I am such a catch, either. Except for #1. I dress like Tarzan.

  9. I like Points 4 (Relate) and 5 (Relax) best.

    After the excitement and passion of dating romance subsides (as it surely will or leading a normal life will be impossible), what goes a long way to sustain a long term relationship over decades has to be a healthy mixture of love and good old friendship (of the best friend variety).

    • “Relate” and “Relax” is always good advice when getting to know people and presenting yourself – be it a date, a job interview, a dinner, a business meeting, or whatever. And it’s an excellent long-term approach, too.

  10. For me it’s about this : Be passionate (not perfect) in your life and be prepared to communicate/share that passion. The other stuff seems secondary..

  11. When it comes to guys, I need all the advice I can get.

  12. It’s a pretty good article! I personally disagree wit hthe “don’t judge him for having too many sexual partners.” I don’t really want to be with a guy that has gone through women like butter on toast. It’s kind of the reverse of telling women not to sleep with guys right away. I also want a man responsible with his sexuality just like men want women to be responsible with their sexuality even if they want to sleep with us.

    I also disagree a tiny bit on the tests! I don’t think you should be testing someone to trick them into messing up. But sometimes asking certain questions or such and testing or “feeling out” a prospective partner can be a good thing.

    But all in all, I liked Josh’s advice.

    • You can be responsible with your sexuality and have a somewhat high number of sexual partners. I mean I’m not saying if he has slept with hundreds of people, but if his number is like 30… that seems like a whole lot, but depending on age and time between it may not be. Plus if he’s clean and has been safe that is in the past. Now he might be more mature and he wants to leave all that in the past and get more serious. He should be judged on who he is and what he wants at the current time. The same goes for women. Well this is how I see it anyway haha to each their own!

      • I agree that you can be responsible with your sexuality and have high numbers. But in most cases, those with high numbers are probably more pleasure seekers in general. I am not saying people with high numbers are bad partners or that seeking pleasure is wrong. I just like a little more disconcernment.

  13. Great article- it’s also important to temper expectations on a first date (this goes for both men and women). First dates by nature are a little awkward, even with good chemistry. You basically want to get just enough information to justify having a second date..

  14. Is this “advice” meant to be satirical?

    • Good question. Satire is hard when reality has devolved into a state of complete silly.

    • Phew. Satire. Okay, if it’s satire i can stop scratching my own eyes out.

    • Why would this be satire? It’s solid advice and if you’re following it and they’re still not calling back for a second date then either it was a really poor match to begin with or they’re players that you probably wouldn’t want anyways.


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