I’m usually a fan of advice based on positivity, but sometimes you need to deal with not so great situations.  I just ran into one of these last night, and I’m going to use it as a springboard for this question:  what do you do when your text flirting falls flat?

Here’s what triggered this…a couple weeks ago I went out with some friends, and met this girl Ashleigh (yes, she had the unusual spelling and made sure I got it right).  Over three bars and many drinks we hit it off, and ended up at my place that night and had fun.  You’d think it’d go somewhere…but it ended up awry.

She forgot some jewelry at my house, so I waited until the following evening and sent a quick teasing text “just found a silver bracelet…so not my style, wonder who’s it could be ;) ”.  For any girl into me, that’d work wonders.  Instead…I got a one-word text of “Whoops”.

For anyone paying attention to the rules of tempo knows that her answering my text with one word is a bad sign.  Still, we did just hook up the night before so perhaps she was playing coy.  I left it on ice for a few days and tried again.

Long story short, I used a few casual pinging texts over the course of the next week and a half.  Each time, I’d get a weak response from her.  Sometimes you need to just grin and bear that time period and keep trying, as she’ll come around.  This time, she didn’t.

So, when you’ve had a good exchange with a girl but then your flirty text is suddenly falling on deaf ears, there are a couple things to keep in mind:
1.  Don’t keep digging your hole.  It’s tempting to keep sending her more texts to try to turn it around, but any time she’s giving you weak responses, go quiet and wait to try again another day.  If you instead keep pushing, you’ll permanently hurt her attraction to you.

2.  You can be persistent…but it must be patient.  It’s one thing to text a girl once or twice a week until either she starts responding positively or you lose interest.  What isn’t cool is trying over and over again, day after day.  A good rule of thumb is this:  wait one day after the first text, then for every text that doesn’t go somewhere, wait an extra day.  So, skip one day…then skip two…then skip three…etc.  This keeps you from going into “OMG stalker territory” in her eyes while giving you a shot at turning it around.

Now, in the story I told you here I followed my own text flirting advice and it didn’t pan out.  That happens.  Just to show you another example, a couple months ago I met this girl at a downtown bar.  The first text I sent her got a lukewarm response, so I waited a day and tried again.  Still a weak response.  I waited two days, and got another so-so reply.  I then waited three days after that…and when I sent her a casual joke, I got a great reply and ended up seeing her later that week.

It turns out she had a boyfriend so we didn’t go anywhere, but by being patiently persistent, I met her and her friends out and ended up dating one of them for a while.  The right kind of low-key pursuit in flirting can work for you, you just have to accept that there’s always going to be randomness in who goes somewhere and who doesn’t.


Interested in how to send flirty texts and be successful with seeing her again? Check out this book, which takes you through everything you need to know about what to text her, when to text, and how to handle her both when she’s already into you and when you have to do some work to get her interested.

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There’s a long standing cliché when it comes to bars and clubs of the so-called pickup line.  Anyone who’s ever heard one–one choice example being “hey baby you must be tired, ’cause you’ve been running in my head all day” knows how awful they are, and completely useless for anyone actually trying to meet girls.  Yet, many people make the same mistake when it comes to flirty text messages, sending something cringe worthy instead of witty and effective.

I went Googling to see what messages I could find posted on the web.  Let’s look at three basic types that I found:

1.  ”I wish I was a teddy bear, that lay upon your bed, so every time you cuddled it, you cuddled me instead.”

Believe it or not, this was the first flirty text I found posted at a website.  It’s just as good as your old-school pickup line.  Read:  absolutely terrible.  It’s a cheesy statement, puts way too much value on her, and unless she absolutely loves you already, it’s going to turn her off completely.  Forever.

Score:  0 out of 5.  Hopeless.

2.  ”Stop thinking about me!:)”

This one has promise, but needs a little work.  The tease behind it is a good one–rather than be gooey and complimentary towards her, it casts the guy as the cool one–but puts too much emotion in.

Note the “!” followed by “:)”…this screams forced joke to the girl.  If you’re going to use something like this, you need more tension.  Look at how it reads without the punctuation:

“Stop thinking about me”

Look too harsh to you?  This would work really well with some girls, but runs the risk of alienating some.  Here’s a happy medium:

“Stop thinking about me ;)

This communicates that yes, you are joking, but without reaching too far emotionally.  Just be sure that if you do use this, lay off on further smileys for a couple texts.

Score:  3 out of 5.  Reaches too hard, but a small tweak will make it much stronger.

3.  ”Those beautiful eyes, that incredible body, such a brain, a sexy mouth, nice smile …. but that is enough about me, tell me how you are?”

This one…is actually good.  Note that it starts as if it’s going to be some cheesy over-the-top compliment, that would be guaranteed to fail, but then ends with the reversal.

Score:  4 out of 5.  The only way to make it better is to tailor it to her using callback humor or an inside joke.

This one hits the right buttons:  the guy is being funny without forcing it, he’s putting her on the spot somewhat, and it’s also noncommittal.  One trap you want to avoid with flirty text messages is sending something that makes it seem like you need her to respond, because if you do that and she doesn’t respond, you lose value in her eyes.

It’s much better to send one-off flirty text messages where if she doesn’t bite, it’s not actually a blow-off.  You were just sending something casual, and it doesn’t matter if she doesn’t respond.  That’s the problem with sending a girl something like “hey, what’s up?”–if she ignores it or takes 8 hours to respond, it’s a clear blow-off to you.  Keep the texts light and funny and you’ll avoid that trap.


Interested in how to send flirty texts and be successful with seeing her again? Check out this book, which takes you through everything you need to know about what to text her, when to text, and how to handle her both when she’s already into you and when you have to do some work to get her interested.

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There is a certain yin and yang to using wit in a flirty text:  a little bit can be funny and attractive, while a lot paints you as approval-seeking.  If a girl is really into you she won’t care, but someone who’s on the fence about seeing and/or dating you can be easily turned off by excessive wit in texting.

The good side of wit is that it can be a funny way to establish contact with a girl.  Let’s say you haven’t texted her for a several days or weeks and you want to reconnect.  Here’s a bad text to send:

Mike:  hey sara, what’s up?

Why is this bad?  Have a look at what not to text for some pointers.  Here’s something more effective, which I used with a girl who I hadn’t talked to for a week after she had gone on a vacation:

Guy:  operation:  igloo mountain is proceeding.  the ice is lined up and a stick barricade forming…just need something to top it off

I sent that one after a recent snowstorm locked me inside my house for a day, and got this response:

Girl:  hahaha!  that’s amazingggg!…guess who had to risk her life in ice for jury duty this morning?

Why did this work?  First off, I had already made a positive impression on her.  Without that, no matter how good you are texting, it’s going to nearly impossible to get her out.  At the same time, she had been on vacation with no cell for a week and the connection was fading.

If I came at her directly, it could have turned her off.  Instead, I sent something with a little wit that looks like a mass text.  This protects me from her “blowing me off” if she ignores it, as it’s not obviously directed at her.   I’ve used that strategy multiple times with tough to reach girls, where I’ll keep sending texts like that every week or two until I catch them in a receptive mood and they bite.  Like going fishing.

Anyway, after that I immediately dialed down the wit…I still bantered a text or two with her, then I got to the point and made plans.

Now then, let’s say I didn’t stop being witty.  If I kept up the igloo joke for another text it might have still worked…but I’ve seen guys (and my younger self) fall into the trap of just keeping the jokes coming, like a one-man laugh track.

That doesn’t work.  Girls may keep giving you lol’s and smiley faces, but the fact is you quickly put yourself into the category of entertainer instead of romantic prospect.  I’m in this to see girls again, and not just in a friendly way, so I’ve learned to temper the wit.

My rule of thumb is I can use a joke or observation to kick off a conversation, and maybe every 2 or 3 texts I can drop another one in if I need to up the energy.  Generally speaking though, if you stick to the basic rules of sending the flirty text you can get optimum results with just a dash of wit and then getting on to planning the meet.


Interested in how to send flirty texts and be successful with seeing her again? Check out this book, which takes you through everything you need to know about what to text her, when to text, and how to handle her both when she’s already into you and when you have to do some work to get her interested.

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I’ve hinted at my feelings about emoticons elsewhere, and it’s time to get into them in detail.  The problem is that many men use them like women, which just doesn’t work…for anyone involved.  They definitely play a role in flirty texts, but you must use them carefully.

The first factor is the simple case of what emoticons to use.  There are a few that no guy over the age of 12 should touch, and others that can be used effectively but sparingly.  Here’s a rundown of some of the most common:

1.  :) — The generic smiley.  This is one that 98% of the time that you want to use it, you really shouldn’t.  It’s not terrible in of itself, as it isn’t as over-the-top cutesy as other smileys, but it rarely gets you anything and risks making you seem too emotional/needy.  The one time I will use it is if I’m picking up a conversation with a girl I haven’t talked to much when I got her number, or if I’m bringing an old phone number back from the dead.

Think of it this way:  the smile on your face as you send that text should be a smile conveyed in words, no symbols needed.

2.  :D — The over-the-top smiley, and all of its brother and sister smileys.  Avoid this like the plague…it’s way too emotionally reaching, and will instantly drop your attraction with most girls.  I’m being serious–it may sound minor to you, but girls will note this.  Even if her every other text uses an extreme smiley, do not use one yourself.

3.  ;) — The wink, which is the one emoticon that has a place in the player’s repertoire.  When it comes to texting, your messages have a high risk of being emotionally flat…you only have 160 characters to work with, and it’s hard to convey sarcasm and teasing well with words alone.

You may use the wink sometimes–no more than once or twice in any one text conversation–when you really need to drive home a tongue-in-cheek comment.  I save it for when I’m teasing her, and occassionally if I need to drive home a joke I’ll break it out.

The art of flirty texts is not complete without emoticons, however, they are a tool best used rarely, and only with certain ones.  The one exception:  if you break a rare smiley that no one else uses, it can have a strong effect and is unlikely to hurt you.  But again, keep it as an occasional spice to your texts rather than the main dish.

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One good question for anyone texting girls is this…when should you text?  Does it matter if it’s 10 AM vs 10 PM?  And does it vary by person?  I say yes to all of these…let’s look at some details.

First off, the times to text depend on the day of the week.  In general, I group it like so:
1.  Monday through Friday afternoon — Work/School time, where you can assume girls are usually at class or earning a living for most of the daytime, and that they probably don’t want to be having 2 AM text exchanges with new guys.

2.  Friday evening through Saturday night — Fun time, as girls with social lives–which include most any attractive girl that you’d want to text–are going to be hitting parties, going clubbing, and generally hanging out with their nearest and dearest.  Which, for our purposes, is not yet you.

3.  Sunday — The transition day, where the rules work a little differently…more to come on that subject.

For work-week texting, you have several options.  I’ve found that texting during the actual working day–say between 10 AM and 4 PM–can be effective with 9 to 5 office workers.  I would not text earlier than 10 nor later than 4, as you run into people who work different shifts and/or will be more worried about either getting settled into work or commuting home rather than talking to you.  For students, this range also holds true as not all of them have morning classes, and texting before 10 can lead to conflicts.

I would generally avoid texting around the end of the workday and through dinner time, which goes from roughly 4 PM to 8 PM for most girls.  They usually are either busy going somewhere, having dinner with or without friends, or generally caught up in something.

That leaves the sweet spot of 8 PM to roughly 11 PM.  For most girls, they’re going to be in the wind-down part of their night by 8, and you can text them with a good chance of response up through 10 to perhaps 11.  I would text no later, unless you’re dealing with a girl who works nights (such as a bartender).

Weekend texting brings a different set of hazards.  As much as no one enjoys games, it’s in your best interests to seem like a guy with a lively nightlife, which means that even if you’re sitting at home watching Lost reruns at 10 PM on a Friday…you don’t want her to know that.

For that reason, I consider texting later than 7 to 8 PM on both Friday and Saturday a bad move, unless you’re using a mass invite or the like to try to meet up with her that night.  That’s a more advanced tactic, so for now, I say stay away from that time slot.  Meanwhile, you can text on the afternoons as normal, which can be useful for setting up that same-night rendevous.

The one other exception is that when you meet a girl that night, you can safely text her at the end (say around 2 AM).  See this article on sending the flirty text for a description of the same-night text.

Lastly, we have Sunday, the day of transitioning from weekend fun to workweek drudgery.  Time-wise, treat this like a work-week:  it’s effective to text either afternoon or late evening, but no later than 11.

Sundays have a very nice perk to them, however:  as they happen at the end of the weekend, where most single girls are still single and probably had a night or two out without meeting cool guys, they tend to be more open to talking to new men in their lives.  For that reason, I will almost always text girls Sunday evenings between 8 to 10 PM, maybe a touch later.  It’s your single best time slot during the week.

Keep these date and time arrangements in mind, and you’ll give your text girls game a boost.  Contacting her at the wrong time–either 7 AM Tuesday morning or midnight on a Friday–will potentially hurt your burgeoning relationship, so pay attention to the time boundaries and enjoy the rewards.

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Maintaining the tempo of texting is important…but before you can get into managing your text message flow, you need to time when to contact her.  Let’s go over that…here’s the scenario:  you’ve just met a cute girl at the bar Friday night, and you want to follow up.  Do you call or text?

You’re reading this site so I’m sure you know I’m going to say “text!”, but there’s a good reason for it.  Calling a girl for your first contact is like going all in on a poker hand:  all your chips are on the table and if she doesn’t return your call, you’re probably done.  On the flip side, texting is like probing for interest…with the right first text, even if she doesn’t answer you can try again later.

Also, most 20-something women (and an increasing number of older ones) are compulsive texters, and are simply more comfortable with it than that nerve-wracking first call.  After all, as scary as it can be for a guy to call her and have to make it into an exciting talk…every attractive girl has had awful drawn-out phone talks to nowhere, and so is cautious about getting into them again.  Like it or not, all men pay the price for those who can’t handle themselves with girls.

Now that we’ve agreed on texting her, the next question is…when?  I love Swingers (the movie, for the culturally clueless ;) as much as the next guy, but the era of waiting “exactly two days” is done.  For girls that you meet in nightlife–ie. bars or clubs–I’ve found your best bet for the first text message is within 24 hours.  

If you meet her at 11 PM on a Friday, you can even send the first one as you go home at last call.  If you’ve met the girl during the day or through friends, you can safely bump that window of time up to 48 hours…but again, I would not drag it out.

I can already hear cries of “but isn’t that needy!”, so let me put this way:  playing super aloof may sound like good advice to guys who used to come on too strong to girls, but it’s a trap of its own making.  When you’ve met a girl with alcohol on the table–which is true for most nightlife and house parties–even if she was into you at the time, there’s a risk of her forgetting you quickly…especially if she’s given her number out to four other guys that night.

Instead, you’re better off sending that first text early…and starting your text flirting on the right foot.  From there, you can get more creative with your timing and content of messages.  At the same time, never forget this:  you text her to get her to meet you out, as real gains are only happening in person.  The flirty text is just another tool on the path to having women in your life, though it’s now a critical one.

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With the rise of flirty texting, the challenge of finding the right notes to hit when texting girls has become crucial to successful dating.  There are a handful of ways to manage your texting, including one of the most important:  tempo.

Tempo is the rhythm of your interaction with a girl.  The kind of tempo you have comes down to who texts who, how long you wait between messages, and how long those messages are.  Let’s look at an example of bad tempo, then I’ll get into the details of it.

Bad Tempo:
guy:  hey cowgirl, what’s up?
girl:  haha hey you, not much. studying, got an early exam
guy:  oh yeah that’s rough, i’m always studying last minute and rushing to get to class. especially in biology! ;)
girl:  yeah me too
guy:  so, what’re you studying?
girl:  english 201, chaucer
guy:  oh yeah I hated that guy.  way too slow reading
girl:  yeah, gotta go, getting late
guy:  oh ok, goodnight, good luck tomorrow!
girl:  (no response)

Painful to read, isn’t it?  I’ll be the first to admit that I had a conversation or two just like that back in the day, and I have a feeling that if you’re here…you can relate ;)  Let’s take a look at what’s wrong with this picture:

1.  Length of texts
At the start of the text, the girl was pacing the guy and sending texts about equally long.  Note that some of his texts were literally almost twice the length of hers.

This might sound minor, but think about it:  looking over this exchange, who wants who more?  Who’s chasing?  As much as it’s frustrating to have to play games like this, with text flirting you need to be careful not to overplay your hand early on.  

When her responses started getting short, he needed to do the same thing…or just go quiet, which leads us to the next point:

2.  The back-and-forth flow
Here the guy texted first…which is usually going to happen, at least until you’ve slept with or at least gone out with the girl in question.  There’s nothing wrong with that, but, when you text first…it becomes important to have her text last.  

In this case, he could have gone silent on almost any of her texts.  The fact that he kept trying to keep the flow going cost him, as his every text got weaker until the end when he wished her well and got no response.  He started fine, but should have stopped after she sent him the negative response of “yeah me too”, which shows she’s not into the conversation.  Anytime you sense the end coming, don’t try to prolong the texting, but instead end it gracefully by going quiet.  It gives you room to recover from mistakes.

3.  Overly emotional
I’ve said it before, but need to keep hammering this one home:  you can’t show more emotion than she does.  Here he got a good reply on his callback humor, but after that, he was the one using ! and ;) while she was sending him flat replies.

There’s a primer on keeping tempo in your flirty text messages…this can literally be the difference between a girl meeting you out or forgetting you completely, so you need to stay on top of it.  Your goal should be to roughly pace her emotional investment and length of messages, while looking to end texting exchanges on a high note–and on your terms.

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Last time we took a hard look at ways to not send flirty texts…and now we’re going to get started with the right way to send a flirty text to a new girl that you just met, say at a bar or party.  Now, I’ll talk about timing when to send this text later…but for now, just understand that you should text relatively fast, within 24 hours for cold approach (ie meeting a new girl at a club) and up to 48 hours for someone you met through friends.

The point of this first text message isn’t to get into a long conversation–we’re going to send her something to cement her memory of us, and also gauge how interested she is right off the bat.  

Alright, so it’s time to send the first text.  What to say?  There are two reliable ways to go…
1.  Callback humor:  any time you have a good flirty interaction with a girl–and if you’re not doing that, then fix that problem before you even worry about texting–you should have a good inside joke or two come up.  For example, if you find out a girl grew up in Texas and used to ride horses…you can nickname her “cowgirl”.  When you send a first text to her, you can use something like “hey cowgirl, better get to bed early…you need to feed bessie in the morning ;)

The trick to good callback humor is to find something that playfully recalls your conversation.  Don’t abuse it however, you should at most use it every other time or so when texting her.  Too many repetitions will play the joke out.

2. The generic non-needy goodbye:  this is a whole order of magnitude weaker than callback humor, but can be used if you have nothing funny lined up but need to make that first text.  I’ve had good success with this tried and true:  ”Nice meeting you, have a good night.  ~(my name)”  

It’s bland as all hell, but has an effective test built right in:  if she won’t bite on this, then you didn’t get enough initial interest on the first meeting to come out for a date anyway.  When she responds, don’t expect much…but the more emotion she puts in her response–such as extra emoticons or punctuation–the better a first impression you put on her.  This will tell you where you stand with her, and you’ll then follow up with something better later on.

There are some of the basics for sending a flirty text to a new girl.  The best approach is to use a little wit and nail some callback humor to her, as when you can reference the conversation in a funny way, it’s going to put her back in social mode and remembering meeting you.  If you can’t do something flirty based on that, your next best approach is the generic–but not overly emotional–polite greeting.  While that won’t build attraction, it will not cost if she’s already interested in you…and will also give you a good idea how likely she is to meet up when you text in the future.

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Here’s the deal:  you met a cute girl at the bar or a party, got her number, and it’s time to text her.  The question is, how do you convey the right flirty attitude without being cheesy or too emotional?  We’re going to take a look at a few elements of the art of good flirty texts.

First off, let’s look at what a good flirty text isn’t.  We’re going to look at some examples of bad texts, with the situation of a guy who just met a girl and is trying to get something going.  Disclaimer:  I don’t pretend to have sent these myself, but I’ve had female friends show me the embarrassing things guys have texted them.

1.  hey sarah, it’s john…we met at Generic Bar #3 fri night.  you seem really cool, we should get a drink

What he’s trying to do: “john” isn’t really sure what to say, so he starts by reminding Sarah where he met her, then he’s complimenting her and asking her out.

Why it doesn’t work:  you should always assume the girl remembers who you are (you did put her name in your phone, right?  if not, start doing that every time you get a number).  Beyond that, going right into flattery and asking her out isn’t going to work unless she’s 99% sure she likes you, and most of the time, the girls you meet at a bar or nightclub is going to take more work than that.

2.  hey grace, great meeting you…you said you like jazz, we should go to that new jazz club on Z St

What he’s trying to do:  our luckless protagonist is starting normal enough with Grace…but then wants to show rapport with her by referencing back to their conversation and using that ask her out.

Why it doesn’t work:  there’s a funny catch-22 with remembering what girls say to you.  On the one hand, they always say they want a guy who pays attention…but on the other, the more details you remember about them early on and then parrot back to them, the more likely they are to cast you into the stalker/creeper role.  Unfair as it is, you want to avoid this.  The only time this text would work is if they had already agreed to go to that jazz club, and even then he’s better off going about it differently.

3.  yo beth, steve here…what’s up?

What he’s trying to do:  casual as can be to start a conversation.  Steve thinks this can lead to a back-and-forth talk, and he doesn’t even have to send something that looks like a flirty text.

Why it doesn’t work:  he’s asking Beth to carry the conversation.  If she’s reasonably into him she may reply…but if she has any doubt, she’s going to ignore this text, and when she would reply, most responses would require him to ask more questions to keep it going.  It’s a weak way to start texting, putting him at a disadvantage from the beginning.  

These examples may or may not seem extreme to you, but I can tell you right now that men I’ve known–and myself in my more naive days–have tried to send flirty texts and instead came up with these.  And yeah, you can write these much better…but if you have the same basic flaws–trying to flatter, trying to force commonalities, and relying on her to make the conversation happen–you’ll still run into problems.  Next time we’ll start getting into just what makes for solid flirty texts and show you a better way.

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