Chapter 16 : My Simple Texting System

If you’ve been following the advice in this book you will be getting a fair amount of phone numbers. Once again, I’m not saying to try to get as many phone numbers as possible. I’m saying that if you put yourself out there you’re going to start meeting a lot more women you have chemistry with and who you’ll want to see again.

Unfortunately though, once a phone number is received, a lot of guys make mistakes that prevent them from ever seeing that woman again. This chapter is meant to highlight the most common mistakes. While there will always be connections that don’t pan out for reasons that have nothing to do with you, by following this advice you’ll be able to ensure that the vast majority of numbers you take (from women you have actual chemistry with) will turn into dates.

Also, you may note that the title of this chapter isn’t “My Simple Calling System.” That’s because texting is more convenient than calling. When you call a woman, it puts her on the spot. She has to be available at that exact moment you call and be ready to have a conversation with someone who probably makes her a little nervous. If you had one of those connections I’ve discussed many times, she probably likes you, and human beings get nervous when they like someone. Texting someone recognizes that they have a busy schedule and allows them to respond when it’s convenient for them.

Also, when a woman is into a guy, she’ll often have her texts to you proofread by at least one of her girlfriends so she can feel more confident about what she’s communicating to you instead of worrying about coming across as “awkward” on the phone. A few women will still prefer phone calls, and they’ll be sure to let you know. If that’s the case then give them a call and simply apply the advice given in this book.

Technology has changed human communication since the dawn of civilization. You may hear someone say, “I don’t like texting, calling is more personal.” When telephones first came out, I’m sure there were some people saying, “Phone calls are so impersonal, just go see the person or write them a charming letter.” I’m not saying that a phone conversation isn’t nice, I’m just saying that an in-person conversation is better and texting is best to set up that interaction.

Despite many guys venting their frustrations about texting women, it’s actually quite simple. If you haven’t embraced it already, now is the time to do so. Here’s how:


The most common mistake guys make when texting is that he feels he needs to win her over and get her to give him enough of a positive response that he feels comfortable asking for a date — just like his concerns over expressing his desire in the first place. He’s ignoring the fact that she already likes him and wants to see him again, indicated by the fact that she gave him her number in the first place. After she sends me two or three texts that show thought and emotion, I’m going to start setting up the date as I describe below.

Your texts should never be sent with the intention to try to get her to like you more; otherwise she’ll start to wonder once again why you’re trying so hard. She’ll eventually give shorter and shorter responses to these attempts, or start ignoring you altogether. Then you wonder where you went wrong and what you could have said to get a stronger response out of her (to get her to make the first move). Meanwhile she simply got tired of waiting for you to ask her out.

Instead of trying to get her to like you more, texts should only be sent for these purposes:

1. To share a little about your day and show her you’re curious about how she’s doing and what she’s up to.

2. To employ the conversation skills (detailed in Section Two) to either react to what she’s saying, share humor, relate your own experiences, or ask deeper questions.

3. To set up a date.


Again, due to archaic custom, it’s typically your job to start the texting. I’ll typically send a text the next day around mid-afternoon (because I’m usually busy with other priorities before then), along the lines of the first point I made directly above. Something like, “I’m loving this weather. You doing anything to enjoy the sunshine?” Every person has different preferences with texting though, and once I send that first text I’ll usually respect her texting preferences while at the same time honoring mine.

The first area I’ll follow a woman’s lead is in timing. If she likes to respond quickly, I’ll tend to respond more quickly in between taking care of whatever other priorities I have for the day. If she takes longer to get back, hours or even waiting until the next day, it doesn’t mean she doesn’t like me, just that she’s busy and that’s her texting preference. I’ll mirror that preference.

Also, some people like to have conversations via text, while others prefer short, quick texts. Once again, I’ll mirror her preferences. If she doesn’t fill in the lulls with additional questions back at me, then I’ll keep my responses shorter and won’t try to continue the conversation after filling in the first one or two lulls — as long as I’ve proposed a date. If she gives longer responses and fills in those gaps, then I’ll enjoy a more conversational text interaction as long as I want to, given my other priorities.



One last mistake that guys often make when it comes to taking care of the logistics is that they don’t confirm the details. He might say, “I’d love to grab coffee with you, are you free on Wednesday? She’ll respond, “I am”, and the guy will reply, “Cool,” or “Sounds good.” He’s excited because he feels like he put himself out there and the date is on. Meanwhile he never actually confirmed that date and she’s wondering if it’s actually on or not. If he lets a couple of days pass before he mentions the date again because he’s nervous that he’ll “mess it up,” then she could very well make other plans, leaving him frustrated that she “flaked” on the date he was looking forward to.

It’s important to confirm every detail. When she says, “I’m free Thursday,” I’ll reply, “Sounds great, I’ll look forward to seeing you then.” That’s a small change, but one that makes a big difference. When she says, “8:00 works for me!” I won’t say, “Sounds great,” but rather I’ll reply, “Sounds great, you’re in my calendar.”

Finally, be sure to confirm the day of. Yes, if you’ve already confirmed the date then there should be no question as to whether it’s happening or not. Yet, we’re human beings. If she doesn’t hear from you the day of, it’s a perfectly normal human reaction to doubt whether it’s on for sure. A simple, “Looking forward to seeing you tonight! Hope you’re having a great day.” is all it takes.

It’s often your job to take care of logistics. Don’t shy away from the task, but instead make her feel like every detail is handled.


When a woman doesn’t respond to your text messages, guys have a tendency to ‘freak out’ and start over-analyzing every little thing that they might have done wrong. As long as you had a genuine connection when you get her number in the first place then her lack of response probably doesn’t have as much to do with anything you did wrong as it has to do with something happening with her. Maybe she had an ex pop back into her life, maybe she lost her phone, maybe she got busy and just forgot, or maybe you spent too much time trying to get her to like you with your texts instead of asking her out.

When a woman doesn’t respond to my text, I’ll wait a bit (mirroring her space if she perfers it) and send something along the lines of, “Hey, is everything alright?” Once again, as long as you had some sort of genuine connection, she’ll usually respond with an apology and the reason behind her lack of reply.

Keep in mind though, sometimes a woman will just fall off the map. It happens. If you’re doing everything right though, you should be going on dates with a very solid majority of numbers that you get. For those minority of women who disappear, after I send my, “Is everything alright” text, I’m sure to give them the space they’re requesting (through their actions) and not text them again. It’s not uncommon for those women to get back to me a month or two later with an explanation of what happened — usually an ex or a super-busy professional life — and an offer to get together. If you show poor social intelligence and ignore her silent requests for space, then you’ll never get these month-later texts.


With these rules in mind, here are some examples of my texts that illustrate them. The most common responses guys have to my texts is “That’s it?” and, “That looks so simple.” When you’re not over-complicating things, it really is simple. These examples aren’t meant to show off or share some secret tricks that I use, but merely to demonstrate how simple and easy this really should be, and that it’s only our insecurities that make it so difficult sometimes.

This quick interaction is an example of what I did when she was already going to be in my neighborhood. Since we had a short time frame, I took care of logistics as quickly as possible:

Me: I’m not going to lie, I was a little hungover today. You up to anything fun? 4:32 PM (Sharing my experience, showing interest in hers)

Amazing Woman: That’s a bummer ;(( I feel great. I’m showing my friend (who I had met the night before, and who also turned out to be a fellow dating coach) around the city and doing a little shopping. 4:35 PM

Me: It’s fine, I’m over it. And that’s fun to do that kind of stuff while she’s in town. You girls going out again tonight? 4:39 PM

Me: And you’re not near Nolita (a popular shopping neighborhood in NYC) by any chance are you? 4:40 PM (I also realize that if she’s doing shopping stuff there’s already a good chance she’s already near me. Also, notice that I’m sending two texts in a row here.)

Amazing Woman: Not sure.. We might in Brooklyn… Have my aunt coming into town tonight to hang out. 4:41 PM

Amazing Woman: Not in Nolita, but that should be our next stop. In maybe an hour. 4:41 PM

Me: Awesome on both accounts. I live right next door to Nolita, we should grab a drink when you guys get here after you’ve hit all the stores you want to hit 4:46 PM (Since I didn’t actually express that I wanted to see her yet I have to do that.)

Amazing Woman: Sounds good ;)) 4:47 PM

Me: Let me know when you’re ready for that drink and I’ll pick a place 4:51 PM

Amazing Woman: Ok 4:52 PM

Amazing Woman: Want to meet up still? 6:44 PM (A little late, but she was shopping – you’ve got to let these things slide.)

Me: Of course. Let’s meet at Spring Lounge on Spring and Mulberry, I’ll leave my place soon 6:47 PM

Amazing Woman: Ok 6:49 PM (Date is on!)

This next interaction is about as close to the “norm” as it gets for me. I’m including it because I wanted to give you plenty of examples of what I do 99% of the time when I text – nothing fancy, just having a normal conversation. At a certain point I’ll stop explaining what I’m doing in each text because it’ll just become too repetitive.

Me: Hey hun, how’s your Saturday going so far? 5:34 PM (Just showing I’m curious about her day.)

Wonderful Woman: Heyy, it’s good, just went to brunch and walked around the village. What about you ? 7:20 PM

Me: That sounds nice, especially in this weather. I grabbed brunch with my friends and we hung out around the city 9:47 PM (I’m empathizing, sharing some of my experience.)

Me: You going out again tonight? 9:47 PM (It’s still the weekend.)

Wonderful Woman: Yea going out for a bit now what about you 11:09 PM

Me: Out for drinks with my friend. What neighborhood are you guys in? 11:54 PM

Wonderful Woman: We are in west village, what about you 12:47 AM

Me: Hey, I was super tired and ended up going home. How was the rest of your night? 3:11 PM (Things didn’t exactly work out that night, so it’s an explanation of my disappearance and more of the same.)

Wonderful Woman: It was fun, just went to houston hall for a bit 3:57 PM

Me: I haven’t been there yet but it looks cool. Did you do anything fun today? 6:20 PM (I didn’t delay this response on purpose or anything, in fact it probably would have been better if I had replied a bit sooner. It just happened to be the case that I was exhausted after finishing a program that weekend and had just woken up from a nap)

Wonderful Woman: My mom and sister were over, so just went to brunch w them. What about you 7:58 PM

Me: Nice, where’d you go? I just had brunch with my friends at coffee shop 8:41 PM

Wonderful Woman: Sounds fun. We went to extra virgin 8:51 PM

Me: I’ve never been but it sounds good on yelp. Did you get the french toast? 9:06 PM (I mean we all have the internet – I’m just showing that I’m interested in what she did that day.)

Wonderful Woman: I didn’t, but I totally regretted it. It looked really amazing. Def get if if you go! 9:09 PM

Me: I don’t know, the basque scramble is calling my name. And I’m busy on Monday, but are you free to grab a drink this Tuesday by any chance? 11:11 PM

Wonderful Woman: Hey, I have dinner plans Tom night, but I could do something later on in the week 10:05 AM

Me: Nice, how does Thursday work for you? 1:38 PM

Me: And how’s your day going so far? 1:39 PM

Wonderful Woman: Thurs could work. Monday is ok, going slow as usual. What about you 5:01 PM

Me: Pretty exciting even though I was trying to take it easy. 7:43 PM

Me: And is there a day that could work better for you than Thursday? 7:44 PM (It’s up to you to nail down the logistics – don’t be afraid to push further if she gives you a less-than-helpful answer.)

Wonderful Woman: Exciting Monday? Thursday is good for me 9:14 PM

Me: It was between a meeting at noon, talking with my grandmother for her birthday, holding a conference call, and attending a bi-weekly meditation group 11:15 PM

Me: And that’s on top of the usual work I had. What does slow as usual entail? And I look forward to Thursday 11:16 PM (Notice how I confirm amid the usual)

Wonderful Woman: Sounds like a busy day. What do you usually write for? Mondays for me always are tough after coming back from the wknd 12:12 PM

Me: It is, and it doesn’t slow down today. Right now my writing efforts are going toward a a book, and yeah, I’m still dragging from my friends being in town 3:10 PM

Me: Got anything exciting going on today? 3:11 PM

Wonderful Woman: Oh that’s nice. What kind of book is it? Just going to dinner later in Les. What about you? 6:37 PM

Me: It’s a book on socializing and communicating effectively. I actually just got done giving a presentation in meatpacking. Where’d you go for dinner? 11:23 PM

Wonderful Woman: Oh wow that sounds really cool. I went to sauce in the Les 11:34 PM

Me: It was fun, but I’m still tired. And I love sauce, their meatballs are the best. What neighborhood do you live in again? 11:52 PM (To help with picking a place that’s convenient for both of us)

Wonderful Woman: I live in the village. What about you? 11:07 AM (The next day)

Me: Just down in Little Italy, which should make picking a place between us for drinks easy. Btw, I’m loving this weather 4:36 PM

Wonderful Woman: That’s nice. I havnt been outside since 7 but I hear its nice ! 6:51 PM

Me: Well I hope it was still pretty warm when you left. What time do you get free tomorrow? 9:09 PM

Wonderful Woman: I’m hoping to be out by around 7 ish. When are you free? 10:22 PM

Me: I should be free by 8, let’s plan on meeting up around then 1:36 AM

Wonderful Woman: 8 might be a little too early. I can do around 9 if that works 11:39 AM

Me: 9 is perfect. Have you been to the Red Bench on Sullivan? 2:27 PM

Wonderful Woman: Never been, that’s Fine though. I hate to be a square but I can’t stay out too long bc I have to get up at 6 Tom :/ 3:05 PM

Me: That’s no problem, we’re just having drinks. We’ll do something more exciting on our second date 4:42 PM

Me: And it should be illegal to make a person wake up that early 5:16 PM

Wonderful Woman: Haha I promised a friend I will go to the gym w her 5:17 PM

Me: That’s not a real friend. Who does that? 5:23 PM

Wonderful Woman: I’ve been trying to go in the morning lately but it’s really hard 5:25 PM

Me: Lunchtime or after work is the way to do it. I’ve tried early before but it never quite worked out for me 5:30 PM

Wonderful Woman: I’ve been doing it for a couple of weeks so we’ll see how it goes 5:46 PM

Me: That’s impressive. I’ll try not to keep you out too late tonight 6:27 PM (Sharing a little sexual feeling, once again just to express my excitement to see her again.)

Wonderful Woman: Hey, I’m running like 10 behind 8:57pm

Me: How dare you! I’m leaving 😉 9:03pm

I chose this final example because it contains an example of her not responding to my text – not because she wasn’t interested in seeing me but just because of natural circumstances. Once again, how would you have reacted to the situation?

Me: Hey you, how’s not doing anything going today? 4:38 PM (An inside joke from the night before.)

Incredible Woman: Not doing anything?! I’ve been on the go since 10 am and will be out until midnight! Funemployment is busy! How are you today? 4:39 PM

Me: Really?! What are you doing that’s taking up 14 hours of your day? 4:43 PM

Me: And I’m having a pretty great day. Did some yoga, wrote a new article, other productive stuff 4:43 PM

Incredible Woman: Nice! Work, exercise, personal, work again 6:16 PM

Incredible Woman: 14 hours goes fast! 6:16 PM

Me: Man, with such a descriptive reply I feel like I’m walking in your shoes 😉 Hope everything goes well 8:53 PM

Incredible Woman: Haha, nothing exciting enough for a narrative. Some good work advice though, happy to share sometime! See you soon? 10:55 PM

Me: I look forward to hearing it. And do you want to go for a walk in central park? 12:16 AM (Que her lack of response.)

Me: That unappealing huh? And here I thought a walk in the park sounded wonderful 6:36 PM (Note that I didn’t take her lack of response personally. I blamed it on her feelings about the park, which is clearly silly.)

Incredible Woman: Oh man, nick. Sorry, such a faux pas, I read your text and forgot to respond. Yes a walk sounds lovely!! When? 🙂 6:49 PM

Me: I figured it had to be something. Everyone loves the park. How does Saturday afternoon work for you? 7:53 PM

Incredible Woman: Probably well. Depends on weather but looks like it should be clear. 8:24 PM

Me: I like how proactive you in checking the weather. How about we plan on Sat afternoon and I’ll just have an alternate activity planned in case the weather sucks 8:42 PM

Incredible Woman: Ok! Sounds fun! 10:07 PM

Me: Oh it’s going to be fun and a half. How’s your Friday going? 3:14 PM

Incredible Woman: So far so good! I went to the Picasso show at the Guggenheim and it was AMAZING. Have you seen it? How’s your day going? 4:33 PM

Me: Damn! I haven’t been to the Guggenheim yet and it was actually on the list of potential indoor activities for tomorrow. Why do you have to be so cultured? 😉 6:07 PM

Me: How was it? And I saw ‘Flight’ and got some work done so it was good. It’s supposed to be sunny tomorrow, should we brave the cold at the park? 6:08 PM

Incredible Woman: Sorry for the delay. I forgot my phone charger. Let’s meet tomorrow around 2:30? 2:13 AM

Incredible Woman: We could also do highline. 11:50 AM

Me: Hey, 2:30 sounds great. And good call on the highline – closer to us, more to do around it, and less of an outdoor commitment on a cold day 11:56 AM

Me: Meet at the beginning? 11:56 AM

Incredible Woman: Great. By the standard? 11:56 AM

Me: Yep, hopefully we can see some naked people 😉 11:57 AM (For the tourist – The Standard Hotel in Meatpacking is famous for people “getting amorous” in broad daylight in the many widows that are very visible from the park below. It’s the first thing a lot of people think of when they think of the hotel, so my comment is appropriate.)

Incredible Woman: I’ll bring my binoculars! 12:17 PM

Me: Just got in a cab, be there soon 2:33 PM

Incredible Woman: Ok I’m on Washington and gansevoort 2:39 PM

Once again, going from a number to a date shouldn’t be a confusing ordeal. It’s really quite simple. There’s no need to be perfect. You just have to demonstrate that you’re a normal person. This isn’t a woman who needs to be won over. You’re simply two people who like each other and want to see each other again. It’s just your job to make that happen.