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.


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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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.


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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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.


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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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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