Most Awkward Text Message Conversation Ever
This couple (who is enough older than I am that we're not peers—I really like them and respect them; we're just not quite peers) who I have been to for a bunch of Shabbos meals invited me for a meal this Shabbos. I happily responded that I was coming. A guy I am friendly with asked if he could tag along. Not being the type who typically hangs out with guys, I felt a little uncomfortable but this guy has helped me find Shabbos meals a bunch of times and is a nice guy, so I said OK and text messaged to ask if he could join the meal. The answer was: "Yes, he can come, but can I be personal and ask how good of a friend he is." At which point, I had to craft a text-message response to answer the unasked question about whether I was dating said guy (which I am not).
New modes of communication. Same awkwardness.