I have had, on multiple occasions, the uncomfortable conversation that always ends with the words “I don’t think of you in that way.” I have sat down with many a guy friend to clarify that we’re just friends. I have explained to guys numerous times that I like to keep my friendships and my relationships separate, and that I don’t date my friends. I always mean it when I say it. I always want to stick to it. But the line between friendships and relationships always seems to blur in my confused little world. Why is “I don’t think of you in that way” so hard for me to say?

There have been several occasions this year where I have had to have this conversation. What troubles me the most is that I can’t seem to avoid it. I’m a huge flirt, especially when I’ve had too many whiskey sours, so I can understand why some guys might get the wrong idea and think I’m interested in more than just a shoulder to rest my head on when the room starts to get spinny. But even with guys I don’t get super flirty with, I still have to have the conversation. It’s always approached one of two ways:

The first is a situation in which I have heavily flirted with, or mildly hooked-up with, a guy friend and I have to explain to him that this doesn’t mean we’re meant to settle down, get married, and procreate. The second situation, and the more annoying one because it’s unavoidable is the, “How come we never hooked up?” conversation. Read More »