Straight off the bat I'm going to assume that you know this guy. If you are inviting strange men over to your house then we may have bigger issues to discuss than text interpretation. However, I'm sensing that you've been seeing this guy a while, that you've had sleepovers, and that you feel relatively comfortable with one another. Even though he's comfortable with you, comfortable enough to cancel, he is being aloof. If he had added in an "I'm so sorry to do this to you" or "I'll make it up to you, promise" that would be one thing; that would indicate he's still hot and heavy for you.
In this case he's beginning to take you for granted. The good news is that he thinks you understanding enough to forgive him. The bad news is that he just expects you to forgive him because he's busy and other things take priority over your time together. It's at this point in dating someone that boundaries begin to get tested. He is seeing if he can get away with canceling on you, setting the precedent that if a friend is in from out of town or he runs into a buddy he can just bail on you and you guys will be cool. You shouldn't confront him by text but exert your power in a different way; by being more aloof and spacious.
REPLY: "Cool. I was thinking of making other plans." This is showing that you're not waiting around for him. He then begins to wonder who you are making plans with, if it's another guy, whether he's missing out, etc. When you do see one another, it's worth probing this issue in person. A simple in-person "I would have been happy for a low key night; it's not really cool with me to break plans last minute" might go a long way.
TEXT: "I'm bartending tonight at Portrait, you should drop by! Should be lots of fun ;)"
This is a mass text. You likely met a guy who is just starting out as a bartender and he's cute, sure, but he doesn't know what he's doing here. He sent this text to every girl he's flirted with lately and half his guy friends (he left out the winky face for them). He doesn't expect you to go. He hopes you will. If you do go he'll definitely sneak you a free drink or five.
At the minimum he wants company at his boring-ass bar. At the maximum he has plans to get you or any other lady that responds to this text drunk enough to stick around until the end of his shift and fool around with him. If you're all for that sort of fling, do it. But know he's not being discriminating. A simple "Hey Jackie. Great to see you last weekend" before launching into the text listed above would mean he wants to see you for real. The existent version means he threw his hook into the water to see if anyone will bite.
REPLY: Nothing. Any guy that's mass texting for company likely isn't that cool. If you think this guy is the one (he isn't) then ask how many friends you can bring; you don't want to be sitting there alone all night waiting for him to have enough time to pay you the attention you deserve.
TEXT: "Send me a pic."
If this is coming from your boyfriend it means that he misses you. He wants to know what you're up to. He's also secretly hoping you'll show something naughty. If this is someone you recently started sleeping with then he wants to see some skin. He's likely had a few drinks to embolden him and he's definitely horny.
In my experience guys never send a text like this if they think they will see the girl that night. If they are going to do that, they can wait and see what they want to see in the flesh. So this guy knows he's not going to see you tonight and is seeking some validation that he's still awesome and can get some (even though he probably just struck out with a girl sitting next to him). If you haven't even slept with the guy texting you he's a creeper and this is a mass text. See last response; he's throwing the hook in the water to see who will bite.
REPLY: If it's your boyfriend? Send him something PG-13 if you're out with the girls. If you're at home and he's out of state send him something more NC-17 (assuming you have had the "If you show these to anyone I will kill you" talk). If it's someone you've recently started sleeping with and you trust them I recommend an old classic: you in a towel fresh out of the shower leads the imagination but doesn't overdo it. If you don't trust them there's no harm in making them send a pic and seeing what happens.
If you're not the sort of girl who does pics, don't do it. Guys shouldn't think they can make these demands anyway. You don't need to text that to him, but you can freely ignore a text like this and they won't get mad; they may in fact get more intrigued. If you haven't even slept with this guy just tell him he's a creeper. Some guys really need to hear that; you'll be doing a service for future women who would otherwise receive this same text from the same dude.
TEXT: "Where were you the last couple of nights? You should have come out with us"
I hate to be the bearer of bad news but, assuming he hasn't been texting you those last couple of nights, this guy forgot you existed. He went out with his friends or maybe even on dates with a girl he now realizes he's not into, forgot to be in touch with you, and only now is figuring out he wants to see you. We do this, from time to time; but only with women we have just started seeing.
I like his move here though; I call it the "Jewish Mother." I call it that, because those readers with Jewish mothers will relate to this story: you're home for the holidays and your mom says, "You never call me." And you say, "You know you can call me first right?" But she's somehow made you feel guilty. That's this guy's move. Instead of acknowledging that he hasn't reached out to you he puts it on you: why haven't you reached out to him? I'm guessing you can see right through it though.
REPLY: If you haven't been impressed with him to date (and that's why you didn't reach out to him) then ignore. He'll likely forget about you again. If you're in a forgiving mood? Try: "Been super busy." The correct and smartest move on his part is to then overtly ask you out sometime soon in order to make it clear that you have in fact been on his mind. The whole "you should know you're always welcome to come out with me and my friends" shtick should be given up alongside your futon. It is for the young and foolish and a good man knows the importance of being forward enough to make a plan with a lady.
TEXT: "Up for a run in 20 min?"
This one is actually quite sweet, if a bit naive. The guy likes you. You're on his mind a lot. He has even started to fantasize about a life with you (I'll get back to that in a minute). The bad news is that the life would involve regular couple's exercise which I personally think is gross. I mean, come on guy, if you're going to be sweating and out of breath at least have the decency to give the lady an orgasm.
I think some ladies may read this text as a guy being inconsiderate. He gives you a twenty minute heads up? That's it? Unless you're both freshmen living down the hall from one another this run ain't happening. If this is a super busy guy you have been on two dates with then this text means the guy is trying to fit you into his life by any means necessary. And he expects you to be sitting waiting for the opportunity to hang when he is able to. That is indeed a douchey move.
I would like to believe that this is a guy you're actually seeing though. You've slept together and live in the same 'hood and have done brunch a lot. A run is something not out of the blue. He's about to go for a run anyway and you've been on his mind and wouldn't it be nice if you guys went for runs together regularly and this became a thing? See? He's in building-a-life-together mode. So I think it's well-intentioned.
REPLY: "Would love that. Have plans today but soon?" Acknowledge that he means well but this is reminding him, gently, that a lady needs more advance notice if they are going to meet a gentleman. And if you're like me and believe couple sweat should be reserved to the bedroom, next time you see him let him down easy and say you take your exercise as a time to clear your head on your own. Or go for a run some time when you've both planned it, but the twenty minutes notice is a no-go.
TEXT: "I could sure use a massage and a fuck from you"
Two assumptions on my part, right off the bat: 1) you've fucked this guy before and 2) at some point the topic of massages came up. If these assumptions are off base and this guy is someone you just met or been on a few dates with ignore this text message entirely; that is sketchy. But if you have fooled around and given each other massages in the past then you have just received a text that I call the "Hail Mary Pass."
The Hail Mary Pass in football is when a player throws the ball in desperation with only a small chance of his teammate catching it and then scoring. In texting, the Hail Mary Pass is when a guy or girl sends the late night booty message without so much as a "How do you do" before it. They mainly come after midnight and at least two drinks deep, when the texter is feeling bold enough to just try and get in bed without any pretense.
The guy sending this sort of text isn't confident it's going to work; in fact he's often sure it's going to fail. But there's something primal about the booty text where he simply can't control himself. He wants you, desperately, and is covering it up with bravado. I'm of the opinion that guys should try and be a little more clever than this sort of message. Not a lot of wooing here. I mean, he's not even offering to massage you back; not a good sign in terms of further reciprocity when you move on to the sex part.
REPLY: If the sex is awesome and you like him? "Come over. But you're giving the massage." Assuming he's actually sorta a nerd and you're not feeling it? An "In your dreams" never goes out of style.
Lodro Rinzler is the author of 'Walk Like a Buddha: Even if Your Boss Sucks, Your Ex is Torturing You, and You're Hungover Again' and the founder of the Institute for Compassionate Leadership