I ask the same thing about women. Women do this wayy more often than men, then that confuses the hell out of us. But for a guy to do so is tricky to say. I used to be pretty shy and still can be till I get to know someone. But, not to the point of bailing on someone. Maybe you all have spent more time texting and a lot less face to face time? If so, you all need to catch up on that. Texting, although you can learn a lot about each other through that, is not a 100% substitute for face to face time? So you all could "know" all about each other, but you don't "know" each other so much. Also, examine your actions. Have you done anything that may have come off as rejection or disinterest? If you did, clarify that. Just make him comfortable to hang out with you. Some people, even some guys, are super sensitive to even the faintest signs of rejection or disinterest or trouble. Girls tend to ignore men or just always say they're busy when they have a guy in their life that they're not interested in (but the guy doesn't know that) Since women do that a lot, most men will become suspicious that "something is up" when the girl doesn't answer a text or phone call or otherwise ignores a guy or says she's busy. Many times these situations are legit but many times just an excuse to not talk to the guy. Us men don't always know which one it is and its taken the wrong way. Some men will be confrontational about it, some, especially men who are shy, will just back off and assume your not interested and move on. Have you tried asking him why he has flaked on you?