Ten Things to Expect When First Dating a Fella

First Date

Josh Bowman provides some insight into the strange and complicated minds of guys during the first few dates.

Note: another response to idatedthatdouche.com

  1. Guys these days are a lot lazier about traditional rules of etiquette. First dates are often hanging out watching a movie, or going to a pub, or just driving around. Doors don’t get opened for you, dinners don’t get paid for. You need to set expectations, and if a guy likes you he will rise to them (as long as your expectations are fairly reasonable).
  2. Men like the chase. Even though every man says “I hate games”, you have to be a bit standoffish at first. Not totally awful, but don’t care too much at the beginning, and you’ll find a guy is more interested. I don’t know…that’s just how our wiring works.
  3. I’ve always been leery about the informal rule that you aren’t supposed to have sex within the first few weeks. I always thought that it shouldn’t matter, and if two people connect then that should be enough. Over time, at least in my experience, I see how that rule makes sense.  Take a bit of time to know somebody before jumping into bed with them, and it will build a stronger base for a relationship. Unless you just want to bone, in which case…go nuts.
  4. Fellas want to create a situation that is as relaxed as possible. First dates are hell sometimes, and I know in my experience the easier I can make it, the better. Relax. Have fun. If it doesn’t work out, who cares? Having that attitude will make the date go better as well.
  5. The reason a lot of guys drink too much in the beginning is because they are nervous. The reason guys say dumb things is because they are nervous. The reason guys “neg” or throw out insults or jibes is because they are nervous. I’m not saying being nervous justifies that behaviour, but that is generally the context for it. I really wish that a lot of guys had other go-tos when nerves hit than being dicks.
  6. I know I said that fellas react well to women who are kind of standoffish, and I want to clarify that. It’s true to a point. If you are carefree, have no problem trading jokes and good-natured insults, and are gonna have fun regardless of who you’re with, that’s a turn on. If you are checking your cell phone and yawning and refusing to talk, that’s terrible.
  7. There’s a trend right now with a lot of men (particularly where I live in Toronto) where we have gotten so many different messages about how to approach women that we are totally clueless. We don’t want to talk to random women because we don’t want to be creeps or jerks. We don’t want to ask out co-workers or friends for the same reason. At the same time, we keep hearing from women that guys never ask them out, and men need to step up, and they never meet eligible, single fellas. All this is to say…you might find that when you first meet a guy you like, or first start dating a guy, he will not be great at talking about what he wants and will be confused and dumb. It helps tremendously to set the precedent and clearly talk about what you want. Some men are good communicators and know exactly what they want…but a lot of men are not.
  8. It is great to want to get married, but there’s something about that conversation that can be really terrifying to a lot of men. I don’t know why, exactly. Fear of commitment, bla bla bla. I don’t think men are afraid of committing, necessarily. I think a lot of men want to be in love. I think there is a lot of sub-conscious anxiety about the wedding itself, and what it represents. My girlfriend explained to me once why engagements and weddings represent a feeling of security for a lot of women. I never thought much about having a wedding (though I have always wanted to have kids), and always saw it as an expensive hassle. I always perceived women who talked about marriage early on in a relationship as just being in love with the idea of marriage, regardless of who the partner is, and that was a huge turn-off. All of this is to say that marriage is an important conversation, but one which is generally had later on in the relationship, and must be handled with some finesse.
  9. Happy men can be deeply depressed. Handsome men can be self-conscious. Strong men can be emotionally volatile or fragile. Quiet men can get angry. There is a lot that might be hidden during the first few dates. Be receptive and open, but know your deal-breakers. If he trusts you, he will let you in.
  10. Dirty jokes are always appreciated.

—Photo Lozbabz/Flickr

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. This is quite a good read, but why do you lambast men for being ‘dumb’ because we receive so many conflicting messages about what women want? Most of the women I know compile ridiculously long, and contradictory, lists of what they want in men (eg he must be sensitive strong dominant but not dominant etc etc x 300). It makes me upset to read so many articles going on about how ‘dumb’ men must be to fulfil these absurd expectations.

  2. Funny… I would easily throw out two-thirds of what I just read here as being complete garbage, and I probably have as much dating success as the rest of my peer group combined. The problem with this type of dating advice is that it assumes that as men, it’s our job as men to try to “impress” women into sleeping with us – albeit, more subtlety than most men are used to. If you buy into the frame presented by the author, all you’ve really proven is that you can follow a script – the dating script – well; until the point that the woman decides it’s OK to sleep with you. This is the exact WRONG way to go about dating.

    The key to dating is to continue to improve yourself to the point where the REAL you is an attractive and sought-after commodity, then use dates as a way both of presenting the real you in the best light possible and screening out women who aren’t interested in what the real you has to offer.

    I never try to overly impress a girl on a first date. 90% of the type its music and drinks at the local jazz bar. I’m excessively flirty and throw a lot of sexual innuendo into conversation. I occasionally drink too much and regularly “neg” the girls I’m with. I hate it when women are even remotely standoffish and will openly call them out on it when I think its happening. Yet, better than two-thirds of the women I’ve dated within the past six months have eventually had sex with me, almost always within the first two dates (and quite often within the first few hours). So yeah, if I pick up that a woman isn’t interested in having sex with me within that time frame, there’s a very good chance that I won’t call back… so no, you couldn’t really say that I “enjoy the chase” either.

    Ultimately, most of the men out there who struggle with dating really just need to “Man Up” a bit (I hate that phrase now because of the way its generally used, but I do think it fits here), get their life together, and figure out what works for them. Unfortunately, there’s is very little in this article that will help either men or women improve their dating success.

  3. Good article. Nice to see Josh’s points mirror my own dating advice. I pretty much agree on all counts, except #10. Dirty jokes on a first date? Could be setting the wrong tone – might save them for date #2. 😉

  4. #1: I think in the interest of weeding out PUAs/RSDers (who hit on tons of women per night and may be carrying STDs from perhaps all the unprotected sex) women have to set some kind of individual standards….otherwise, you are just some random face in the crowd that he may think is too easy, too drunk, or too stupid to see through The Game….

    Saying “no” more often will save you a lot of heartache in the end…if he is serious, he will jump through hoops to get you….

    • Mike Testosterone levels usually start to declined sometime after age 30, and continue a steady decline from that point forward. Many of us in the anti-aging field have embraced the concept of “hormonal optimization” in this philosophy of treatment, a says:

      He might also interpret the hoops as you not liking him. Then go off and find a woman who doesn’t make him jump through hoops.

    • I kind of agree, I don’t expect to be treated like a princess but I’ve wasted SO much time in my life on guys who just want to hang out and be pals and have some casual sexy-sex when the mood hits, and the relationship ends up being a complete dead end and a total waste of my time and energy.

      It doesn’t meant you have to take me on an expensive date. We can go to the farmer’s market or a walk in the park. But make it seem like you are interested in actual you know, going on a DATE with me.

    • The other thing is, if after the first couple of dates, you decide I am not right for you, then do me a favor and end it. Don’t string me along with casual hanging-out non-dates for months and then finally tell me (after I push you) that you don’t see the relationship going anywhere.

      • I agree with you, Sarah… my BF and I were both quite poor in grad school but he made the effort to surprise me (ie., blanket and a bottle of wine in a low lit hallway at school during a study break) or to give me something special from him (ie., a prized black and white photo taken in Central Park that he took and developed himself)….

        He may have paid for those burgers in the pub, but I treated him to the fancy white tablecloth restaurant later on when I saw how serious he was….

  5. Just a metalhead says:

    I won’t go at length about this article, there’s a lot true in it, but…

    “Men like the chase. Even though every man says “I hate games”, you have to be a bit standoffish at first. Not totally awful, but don’t care too much at the beginning, and you’ll find a guy is more interested. I don’t know…that’s just how our wiring works. ”

    No, just no. Wait, not just no, but NO!!!

    I hate the chase. I hate the feeling that building a relationship is only on me, that I have to convince the girl that I’m worth her time while she seems not interested at all in building a relationship with me. When women act standoffish, I don’t start thinking “she’s playing hard to get, me want chase, me work harder”, I’m thinking “she’s not interested and she’s just too polite to tell me off right now, time to disengage”.

    I get that some guys like the chase and the whole dating ritual. Fine with them, to each his own. But I think those people, they’re not serious. They’re in for the “game”, not for what it brings. They won’t settle long in a relationship before they want to break off to start the game again. Men who are serious and who are looking for love, and not just looking for a thrill, they hate the game. If they could just go to sleep and wake up next to a girlfriend, they’d love that.

    • Well put. I stopped reading to come down and respond to that point.

      • A Woman on GoodMen says:

        I am glad to read that – as a woman I hate that whole one-sided chase thing as well… yes I like to be pursued, in that I like having someone going out of his way to express to me that he finds me attractive and fascinating, but I LIKE TO DO THAT TOO. I hate feeling like I am supposed to be standoffish and pretend I can take a guy or leave him when what I want to do is plant a huge kiss on him the moment I see his sweet face! Everyone likes to know that they are attractive; why withhold that??

        • @A Woman—

          You have to withhold and be standoffish to weed out the jerks who wear the mask of charm… It’s called “shit-testing”…. It helps you to quickly identify who is not worth your precious time and affection…. If he is critical or saying something rude ( even as a “joke”), then that helps you to back up and keep your distance…. Stuff like that just gets worse if you allow him to get away with it with you….

  6. First things first: Wonderful article. Definitely agree with just about all of it.

    Regarding your initial point: For me, its not so much that I’m lazy. I’m just sick of the hypocracy that surrounds those traditional rules. The ones that all but demand that I see my date as confirmed, divine, and royalty at almost the very instant of my meeting her while being subjected to an indefinite line of test after test after test of my own worth. For that reason alone: Yes, I would prefer to be in a coffeeshop or pub setting for the first couple of dates so I can show the woman that I’m not a creep, but also make sure she’s not a spoiled, im-so-entitled, diva before being jumped through too many hoops.

    All women talk about being “Ladies”. All I ask of them is that they make some effort to actually prove it, BEFORE seeking out all of the rights and privileges they’d expect to come with the title.

  7. Hi Josh, thanks for your article.

    As a woman, I have experienced all of the things above. Going slow, going fast, and to this date what i have also found it take a lot of luck to be in the right place, right time with the right one.

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