Never Run Out Of Things To Talk About

« Previous 1 2 3 View All Next »

Normally on Wednesdays, I run your questions for Ask Dr. NerdLove and try to help you all out with your relationship issues. Sometimes, however, I get a letter that’s a perfect segue into a topic I’ve been meaning to cover for a while. Today’s writer, frequent commentator Ancom brings up a common set of problems that I hear about with great regularity from my readers: how you avoid running out of things to talk about with someone you’ve just met and – importantly – how to transition from “great conversation” to “getting the number” and  “asking them out on a date”.

Ancom provides some specific examples of what hasn’t been working, as well as an example of some of the game he’s been spinning, so we’re going to be taking this in more of a Post Mortem style than the usual Ask Dr. NerdLove’s.

Strap in folks, it’s gonna be a long one.

Hey Doc,

I recently found your site and I’m impressed by your tendency to cut to the chase. Let’s hope you can help me with something I’ve tried to resolve on numerous PUA sites prior to coming here, because I have a very big problem that I’d really appreciate some input on.

First off, I’m 28 and I’ve never really had a problem landing a relationship or a ONS. I have a pretty great job in addition to having a good life and taking good care of myself, so I always manage to bump into women who can sort of “sense” this from the way I carry myself, and they tend to be willing to meet me without me having to do all too much work.

For future reference: starting off a letter like this generally makes it sound like you’re trying to brag – and then when you get into your problem, it calls this part into question.

However, when it comes to actively carrying a conversation with women, I’m completely unable to do it regardless of the sitaution. It’s really frustrating for me because I feel like I’m missing out on an important part of life that everyone else seem to have no problem with, and it’s preventing me from hooking up with people I’m interested in.

Well, not to put too fine a point on it but… you are. If you’re going to be putting yourself out in the dating market, whether you’re looking to get laid that night or if you’re looking for something long-term, you need to be able to talk to women. I can’t over-emphasize the power of conversation as a tool for building attraction; it’s part of how we find commonalities with one another and how we bond on an intellectual and emotional level. There’s a lot to be said for pure physical attraction, but even the studliest of Studly GoodNights can only get so far before they have to open their damn mouths.

I’ve looked all over the web for a solution and feel like I’ve tried every suggestion in the book, but they all seem to have major flaws.

For example:

1) I’ve tried talking to women like I’d talk to a friend or any other person, but the social dynamics between two strangers are too different from the social dynamics between two friends, and I find that despite being friendly, inviting and making non-threatening casual observations, I never really get a reaction from women beside a courteous laughter or yet another question (which leaves me back at square one of having to keep talking). With a friend you’re just talking about boring day-to-day stuff. It’s not something you’d want to tell a stranger.

First of all: non-threatening casual observations? I’m going to presume that you mean “observations that aren’t of a pointedly sexual nature for fear of making the person I’m talking to uncomfortable” rather than “That’s a nice dress! I bet the material would absorb a LOT of blood if I were to stab you later.” It’s good to make a point of avoiding coming across as “creepy” by accident, but you’re making a classic mistake here.

You seem to assume that the social dynamics of the situation are binary: either you’re talking to a friend – in which case must stick to strictly boring, platonic topics – or you’re talking to someone whom you want to bone and therefore have license to flirt. Now, I don’t know about you, but my friends and I talk about a lot more than just boring “here’s what I did today” stuff. We swap stories, we bullshit, we commiserate about bad days, annoying co-workers, joke around, make plans, discuss philosophical ideas (which may look like geeking out about movies and comics, but I assure you carries weighty metaphorical subtext… weighty, I say!). Occasionally we talk about serious matters: relationship concerns, plans for the future, things we’re worried about. It’s almost never boring unless we need to talk about a boring topic; we wouldn’t be friends if we bored each other after all.

What this sounds like to me is that when you’re talking to a woman “like she’s a friend” is that you’re not expressing interest or flirting; you’re keeping it strictly to small talk, which is profoundly unsexy. If this is someone who might be interested in you, she’s going to be wondering why you’re not giving her anything to work with – it’s hard to figure out whether a guy likes you or not when he’s only talking about the weather or his job.

Second: If she’s asking you questions, that’s generally a good sign that she’s interested in what you have to say.  This is your opportunity to tell some stories to let this person know who you are and why she should want to get to know you. This is where you get to brag a little, in an amusing and charming fashion. You want to show off that you’re a cool person with a lot going on in his life and she would be crazy if she didn’t want to be a part of it.

"Wow, I had no idea library science could be that interesting! And did I mention I *love* tweed?"

2) I’ve tried using canned stories mixed with some questions and casual talk. This works to some extent, but that only gets me so far. How am I going to make that last for 3-6 hours?!

When you say “canned stories”, I’m assuming that you mean stories you’ve told enough times that you could tell them in your sleep, rather than using pre-generated routines that you’ve picked up from PUA sites. While there is some value to the canned routines that some PUA schools advocate – mostly in learning the rhythms and mechanics of a good story and how to hit certain emotional switches- trying to use somebody else’s material is usually a substitute for having a personality and lifestyle that women find attractive.

The way you make this last three to six hours is by being interesting to talk to. How do you do that?

Well, to start with, be interested in what she has to say. This means being an active listener; you need to do more than make the “uh huh” noises, you need to be asking questions and paraphrasing what she said in your own words to make sure you caught everything. You use what she says as a springboard to other topics, either through a transitionary phrase like “you know, that’s like this one time I…” or “So if you did X, have you ever done Y?” You can also ask open-ended questions like “So what are you passionate about?”

3) I’ve tried just speaking whatever comes to mind, but it tends to just dwindle into a lot of casual comments and it has the same drawback as method #1 (which is I get short answers and have to talk even more to make up for that).

There’s a lot to be said for observational topics, but only a) if it’s not obvious that you’re desperately casting about to find something to fill the silence with and b) you can use it to springboard to an actual conversation. Personally, I like people-watching; you have any number of ways of segueing into new subjects – fashion, lifestyle choices, even just commenting on their actions. I saved one date from a painfully awkward “what do we do now” moment followed by a good-night handshake by starting running commentary about another couple that was VERY clearly on a first date and using it as a parallel to our own. The trick is to bring the conversation to a place where the two of you can learn about each other.

Also: if all you’re getting are short, clipped responses, odds are that the person you’re talking to is just not that into you. Odds are good that she’s just trying to run down the clock until the social contract says that she can leave without causing offense. The more interested a person is in you, the more they’re going to have to say and the more they’re going to show interest in what you have to say.

"I'm fascinated. Really."

4) I’ve tried the chode way of just going interview mode on her, asking questions as well as answering hers. I’ve even tried being genuinely interested in what she says, practicing active listening and all, but in the end it’s just an exchange of questions going back and forth. BO-RING.

I have nothing to say here. I’m just going to pause for a moment and just marvel at the idea of “being genuinely interested in what she says” as a desperation tactic.

5) I live an interesting life and supposedly that is supposed to be the source of anecdotes you can tell people or the relations you can draw between what women are telling you and what you’ve previously experienced, but I don’t feel this way at all. As soon as I have done something, I don’t think about it anymore. I don’t feel a need to tell people about what I’ve done. There’s nothing interesting about having gone skiing, surfing, hiking, clubbing etc. What am I supposed to do? Chime in and go “Yeah I went clubbing too last weekend too! A drunk guy puked on me.” I’ve tried every imaginable variation of relating to what she’s saying, and there’s nothing interesting I can respond with. DOU-BLE BO-RING.

Well here’s your problem: you don’t seem engaged in your own life. If you’re living an interesting life, then why wouldn’t you think about the things you’ve done after you’ve done them? There’s more to an interesting life than just going down a checklist of “cool” activities – the point of collecting experiences and memories is to experience them and share them with other people afterwards. And you can’t do that if you never think about it again afterwards.

It’s about more than just having done something; it’s about how it made you feel and what it made you feel. To take an example from my life, I visited Cambodia a few years back and got a chance to do things I never thought I’d do, including exploring a ruined temple in the jungle. What I took away from it was more than just “yup, that was cool,” it was how humid it was in the jungle and how loud it was thanks to all the birds and insects. It was about feeling as though I was walking through every single adventure fantasy I had watching Indiana Jones as a kid and trying not to yell “Throw me the idol, I throw you the whip!”. It was about the way my stomach contracted and my nuts crawled up into my abdominal cavity when I realized that I’d walked into a live minefield and had to pick my way back very fucking carefully. It was about characters, like the little Cambodian urchin who kept trying to engage me in conversation and sell me cheap crap when I was busy trying to flirt with a cute backpacker while watching the sun set from the top of a ziggurat.

Now granted, this is a bit of an extreme example. Not everything has to be an epic tale of adventure and danger in exotic lands in order to be interesting. The seemingly mundane can be interesting, even enthralling if you sell it properly. This means being in touch with yourself and willing to share it with the person you’re talking to.

5b) Even though my life is full of events, not every activity is going to result in an interesting anecdote. In fact, I feel like they never do, and if they do, it’s only something mildly entertaining. I’ve also read that even if your stories aren’t that interesting to you, you can still deliver them with passion. I find this to not be true at all. Even if I convey an experience with both emotion and passion, the other person still won’t have much to say about it and you’ll be left with an “oh cool” or just another question fired back in your direction since she doesn’t have anything to say about your story.

It doesn’t always have to be about X thing happened while you were doing Y activity with Z.

To use one of your examples: let’s talk about skiing. If there’s nothing exciting or interesting about skiing, you’re doing it wrong.


Now, maybe there was something crazy that happened while you were on a ski-lift or you watched somebody have an epic wipeout. But let’s say it didn’t last time. What do you talk about then? Well, to start with, what is it that you like about skiing? How does it feel to be rushing down the side of a mountain with a couple of planks strapped to your feet and the only thing between you and sudden death is your ability to shift your weight? Do you like carving trails in fresh champagne powder, or do you prefer hurtling over moguls. Are you a moderate skiier or do you like taking on double black slopes? Or perhaps you like the effortless gliding of cross-country skiing, the silence of the snowy air and the way that you almost fall into a meditative trance while you’re traversing a field or forest.

Even the example you mentioned about going to a club and somebody getting drunk and puking on you is potentially a funny anecdote to share if you know how to sell it. Build the tension by describing what was happening before you got puked on and how you saw this person headed your way.Create characters – sway back and forth when you’re describing how the drunk walked, speak with an exaggerated slur. What happened afterwards? Did they fall over? Get ejected by the bouncer? Offer to buy you a drink then stumble into a crowd of onlookers?

So that about sums it up for what I’ve tried up until this point. In order to give you an idea of what I’m working with, let me also give you a personal example from last weekend:

And now we enter into Post Mortem territory. I’m going to break some of this down for the other readers – who would get some benefit from it – as well as pointing out where you dun goofed.

I’m at a small bar, and a woman walks up and accidently brushes against me. I jokingly tell her to keep her hands off. She laughs.

So this is a good way to start, For those of you keeping track at home, Ancom’s opener is to jokingly reframe this woman bumping into him as her as trying to get into his pants; she’s clearly willing to play along with it since she laughs instead of fighting it. This implies that she’s at least a little interested in him – or finds him amusing, which is actually close enough for government work. Now to be sure: this is something that requires a certain level of social calibration, because it’s incredibly easy to come off as a dickbag instead of somebody making a joke. But it does set up the situation as potentially sexual rather than, say, becoming platonic BFFs.

I take that as an all-clear for demanding that she at least buys me a drink before she starts groping me. Said and done. She gets me a drink, and I ask who she’s here with.

Now here’s where things get a little dodgy; what Ancom is doing is testing for compliance by demanding that she do something for him. This is a technique that PUAs use to reinforce the frame – she’s seeking his approval by doing what he asks – as well as check how into him she may be. The more interested someone is in you, the more likely they are to do something you ask; sometimes it’s as simple as “tell me something cool about yourself” or “keep me company while I get a drink”. Sometimes it’s “buy me a drink”.

Because there's nothing sexier than someone demanding you bribe them for the privilege of their company.

Now, demanding that she buy him a drink right off the bat is actually pushing pretty damn hard pretty damn fast; he’s demanding a high level of compliance from someone he’s literally just met. This not something I would advocate trying 99.9% of the time. It takes a high level of social calibration to do something like this without being an asshole, and the situations where it would be socially appropriate are pretty thin on the ground. You can pretty much only get away with trying this in singles bars and clubs – places where it’s generally understood that the purpose of being there is to meet (and sleep with) new people.

I’d would run with saying that she should at least introduce herself before she starts groping me – still pinging for a certain amount of attraction and maintaining a frame that she was groping me rather than just trying to get to the bar. Same result, but far less likely to repulse someone who might otherwise be interested in you.

Now that being said, she does seem to be attracted, since she actually does buy a drink.

 She tells me she’s having an after work with some friends. I ask what she does for a living, and she says she’s a receptionist. I tell her that my mother always warned me about receptionists because they’re bad news.

OK Ancom, here you’re starting to push pretty hard on the sexual framing and it’s really unnecessary. She’s already leapt through a couple major hoops to show that she’s into you. It really starts coming across as trying too hard to establish a point and you start risking turning her off. Plus, “Mother always warned me about receptionists”? This isn’t even that clever as a frame; something like this is going to make even people who’re already attracted to you stop and think “What?” and kill any forward momentum dead.

She laughs again and asks me why I’m here. I tell her I came with some friends.


At this point I honestly don’t know how to proceed. I feel like I have zero information that I want to convey to her. I literally don’t know what to say. Can you please help me? This is driving me nuts, and it’s seriously keeping me from meeting a lot of women I would love to be in the company of.

Well, there’re two different issues here. First of all, you were pounding on the “you’re a sexual predator” button pretty hard, which was defining the conversation you were having; when she’s asking you why you’re here, she’s asking what your motivation (as though you hadn’t been telegraphing them pretty blatantly) was for being at that bar, that night. It’s an opportunity to flirt and keep the sexual charge going if she’s that into you already. You want to keep the thread going: “Well, I thought it might not be a bad night to be groped by an attractive stranger,” “Thought I’d get a few drinks and make some bad decisions.” That sort of thing.

Secondly, telling her that you’re here with friends is A) answering a question she didn’t ask B) pretty damn incongruous to the tone you were setting. You’ve gone from flirting to “Yup, here with my buddies.” Not even “my friends are taking me out for a drink because we’re celebrating $AWESOME_THING tonight.” Just “Out with friends.”

What do you want to say? Well, since you were looking to get laid that night, what you wanted to convey was enough about being a cool person to justify her being interested in potentially going home with you. You’d want to find out more about her in order to justify (to her mind, if nothing else) your attraction to her. You would want to find out the potential logistics for that night – did she drive her own car, or did she ride with somebody else? Does she have somewhere to be the next morning that would preclude going home with someone?

If this were someone you might’ve been interested in taking out for a date rather than banging right then and there, you might have wanted to look for common – or at least complimentary – interests by sharing some stories and experiences of your own and asking questions from her. You might want to seed a potential date early on by talking about a cool thing you like to do, then later on mentioning that you’re planning on doing $COOL_THING later that week and she should come with you, then get her number so you can follow up later.

The problem I’m seeing in what you’ve described to me is that you’re trying to get a lot of result for very little effort; you’re not really that interested in getting to know the people you’re talking to as much as progressing down the flow-chart to the desired end point. Hell, you don’t seem all that interested in your own life. Spend a little more time looking to connect on more than a surface level and you’ll find you’re having less of a problem with running out of things to say.

« Previous 1 2 3 View All Next »

Pages: 1 2 3