Mateo not only struggled to start conversations, he also felt lost whenever a lull or “awkward silence” fell over any interactions he did manage to get going. He used the same excuse of “not knowing what to say” — when in fact he just wasn’t asking himself the right question.

Mateo was trying to be interesting, trying to fill the silences with whatever he thought she would like the most or what would be the cleverest thing he could say. Once again, it’s better to be interested than interesting. Trying to impress her with the most interesting thing you can say will only make you look desperate and keep you awkwardly in your head instead of holding space and being present in the moment.

Instead of asking himself, “What can I say that will be interesting?” during a pause in conversation, the only question Mateo needed to answer was, “How can I show her I’m interested?” When you reframe the question in the correct light, the answer becomes much clearer.


Every conversation reaches a lull. A topic is introduced, you both chat back and forth for a number of minutes, relating and asking more personal questions, until you reach a point where no one has anything else to say on that conversational thread (this could take 2 minutes or an hour). At this point, someone has to introduce a new topic or “push the conversation forward” in order for it to continue.

You don’t want to be the one to do this too often, otherwise the conversation turns into an interview. She’ll start to contribute less and less while you feel as though you’re doing all of the “work” to keep the interaction going.

At the same time, she shouldn’t be pushing the conversation forward every time, lest she gets the impression that you’re not interested in continuing to talk to her and that she’s doing all of the work.

Mateo thought he was losing conversations because he wasn’t interesting enough — but in reality the women he would speak to lost interest because they didn’t think he was actually interested in them.

Questions such as “So where are you from?” are often spoken of disparagingly in the dating advice industry as something to avoid at all costs for being too boring and common, but they’re the questions that most commonly come out of my mouth. There’s a reason why we have these established go-to’s — questions like “where are you from” are a good way to get to know about someone you just met and show interest in the other person.

The problem comes in when guys just fire them off one after another, not because they’re actually interested in getting to know her better, but because they’re just trying to keep the conversation going as long as possible, hoping to hit on a topic she’ll like. These questions aren’t meant to set you apart — the fact that you’re actually interested in her responses and listening emotionally instead of trying to say the “right” thing will do that.

When I say, “Hey, how’s it going?” it’s not just something I say to get a conversation started, I actually want to know how they’re doing in that moment.

“What are you (guys) up to tonight (today)?” or “how are you enjoying the party?” will usually yield a half-assed response unless you actually care what they’re doing.

If you say, “where are you from?” as a way to elicit information that you can use to continue the conversation then she’ll probably start writing you off as just another typical guy. But if you genuinely enjoy talking about growing up in different parts of the world and want to get to know her better when you ask the same question, then she’ll immediately feel that and know you’re one of the guys that she rarely gets to meet.

Also important: do not to rush to fill those first couple lulls either. This just sends the same message that you don’t actually care about the conversation and are just trying to make it last longer or are desperately trying to meet some agenda. Instead, take a moment or three to emotionally reflect on what was just discussed and possibly share those feelings with her through eye contact before continuing the conversation. You’ll probably be surprised as well, by the number of times she says something else when you give her the space to do so.

You don’t approach conversations with friends with this mindset: “what do I say that they’ll like talking about?” That’s simply another rut your brain has developed to avoid being vulnerable with your feelings. Instead, when you feel your nerves rising in a conversation, simply be present with that excitement and express your genuine interest in the other person.

When you’re with your friend and you actually want to know what’s going on in their life you might say, “so what’s going on with you?” The words don’t matter, all that matters is the feeling that you care. It’s no different with a person you just met. It doesn’t have to be fancy, it just has to be real.

While genuine interest is the catalyst for the interaction to continue, as noted above, it’s still important not to turn the conversation into an interview. If she hasn’t filled in the first or second lull I’ll leave it to her to push the conversation forward the next time.

Letting the silence go can be incredibly nerve wracking when the other person intimidates you, and five seconds can feel like five minutes. You may be afraid the other person will get bored or feel awkward and not want to continue the conversation. In reality, while they’ll certainly feel more tension in the silence, the worst thing you can do is show that it’s too much for you by talking too much or retreating back onto your head.

Instead, remind yourself that it’s not your sole responsibility to make the conversation happen. Hold space for those nervous feelings and embrace them, and look at her, fully comfortable in the silence with a feeling of, “I can’t think of anything to say. I still like talking with you. What are wegoing to do about this?”

If she says, “what?” to break the tension you can always respond with some variation of those feelings. She’ll most likely push the conversation forward if you’ve been in tune with her feelings up to this point whatsoever. If she doesn’t, it happens, no big deal, and it’s time to start thinking about employing the warm goodbye and ending the interaction.

This is precisely where Adam was going wrong. He was incredible at keeping a conversation going — one of the best I’d ever seen. I’m pretty sure there was never a hint of silence in any of his conversations because he always had something to say to fill it in. He was a good listener and had no problem really being interested in other people. The problem was that Adam never allowed her to contribute to the conversation as well, often interrupting her before she was about to say something, and thus he was unwittingly sending the message, “I’m more interested in me than you.”

Adam happens to be blind, and so he couldn’t get the normal visual feedback that lets us know the other person is still ‘with us’. Without that visual feedback he feared that if he wasn’t constantly getting verbal feedback than she would lose interest in the conversation. I had Adam focus on slowing down — holding space for his feelings instead of reacting to them out of fear with more words — and not always pushing the conversation forward after the first or second time he’s done that. He did so, and the first time the woman he was speaking to filled that silence and showed him that he didn’t have to do all the work, it was a game-changer.

Just like Adam and Mateo, you need to relax and take the pressure off yourself. Instead of stressing yourself out over having the right thing to say — whether that fear drives you to silence or blabbing — start asking yourself the right question: “How do I show her I’m interested in who she is and what she has to say?” You’ll be surprised at how easy holding a conversation actually is.



Fantastic questions for this week:


  • How can I stop daydreaming about a girl after I have a good interaction.
  • If a woman wants to have sex on a first date, should you always go for it?
  • How long does it take to get over a serious breakup, and what are more specific ways I can speed up the process?
  • How do you deal with shy girls in nightclubs when the conversation isn’t really flowing?
  • How do you set/control the frame in a conversation?
  • How do I get over my fear of STD’s?
  • What do you do when you run out of things to say?
  • What do I do if a girl checks out my Facebook profile and seems distant afterward?

Downloadable Audio



Questions for this week include:


  • She has a test coming up, and isn’t going on any dates until it’s over, when/what should I text her?
  • I have trouble trying to create rapport via text, should I call instead?
  • Even though I try to get girls to talk, it feels like they always put the onus of being interesting back on me, what should I do?
  • What’s the biggest difference between college game and real life?
  • Do nice guys really finish last?
  • You say your goal is to get her talking, but sometimes I get called out for not talking enough. What should I do?
  • I’m feeling “numb” after a bad breakup, is this normal?
  • A girl said to me: “you can’t handle me” – how would you respond to this?
  • What do I do if she doesn’t fill in the “lull” in conversation?
  • How do you “pick up older women?
  • How does growing up with divorce affect your love life?
  • Any advice for online dating?
  • I may have ruined things with a girl I liked because I was too afraid to get sexual on our first date – any way I can recover?
  • How does “daygame” differ from “night game”?
  • How can I bring women I’m really attracted to into my social circle when my friends can be embarrassing?
  • How can I be “dominant” in a mixed group of girls and guys?
  • How do you deal with socially dominant women?
  • Is there any way to make a powerful impression over text?

(Downloadable Audio)


You sent me your questions, both ahead of time and through the youtube comment box, and I answered them live. Here’s what happened last night in case you missed it:

(A list of the questions answered, and the downloadable audio can be found below the video)

  • I always get better responses from girls during the day than at night. What’s going on?
  • This girl seems colder when I’m going for the second date, what should I do? (Text examples given)
  • Who should pay for a date?
  • I’m a smaller guy and people seem to pick on me. What should I do?
  • How do you know you’ve found “the one”?
  • How can I not give out the vibe that I’m only going out to talk to girls?
  • What do you think about getting back with your ex?
  • This girl I’m seeing is also seeing another guy. How can I get her to pick me over him?
  • What do you do when girls react to your work negatively?
  • Thoughts on “direct vs indirect”?

Downloadable Audio


Lot’s of great questions this week. Enjoy!

(List of questions and downloadable audio found after the video)

  • I often lose interest in a girl after sleeping with her, am I a bad person?
  • Should I be using “cocky comedy”?
  • How do I get a girl off her cell phone?
  • How do you get sexual physically?
  • How do I keep things on the “DL” with a girl from work?
  • Should I talk to a girl while she’s in a group or on the move?
  • There’s not much to do in my town, how do I keep dates from turning monotonous?

Click for Downloadable Audio