I have been talking to someone from work (texting by day, sexting by night) every day for about six months now. And just recently we hooked up while his girlfriend was on vacation. Why is he keeping up this “relationship” with me? And why am I being naive enough to go along with it?

Oh, sweetie. My heart is breaking for you. I know it may seem like this guy is perfect—like every long text message chain about esoteric topics makes you two soul mates, that every late­–night passion session leaves you burning for more. But I’m going to be blunt with you: stop talking to this douchebag. Seriously. Just stop. Cold turkey. It’s that simple.

Now I know you’re saying, “But Miss Cassandra! Everything about him is amazing/splendid/fantastic/other adjectives!” Tell that to his girlfriend. It is fundamentally true that if a man cheats with you, he will cheat on you.

As to why he’s keeping up this relationship with you­—and you were correct, this is a relationship—I neither know nor care. He’s likely bored in his relationship with his girlfriend, or he enjoys the sneaking around. Quite possibly you both offer him different things and he feels conflicted. That doesn’t excuse his behavior. And one of you needs to realize that.

You aren’t naive. Not really. You actually knew what you had to do long ago. You just needed someone to tell you directly, which is why you reached out to me. Miss Cassandra’s here to give you the swift kick you need, hon. Good luck.

But what about the stuff that gets up around the sides of condoms?

While the astute reader will realize that this is in fact a reference to the popular HBO series “Girls,” it’s a question that most hypochondriacs and nymphomaniacs (which, I would guess, is a large part of Miss Cassandra’s readership) will shudder at.

The so–called “stuff that gets up around the sides” can mean one of two things. The first is condom leakage (I know, it’s just as gross as it sounds). But don’t worry, condom leakage only happens when they are put on wrong or when your partner is not hard, which probably means there are some other problems going on as well (very Marnie and Elijah­—if you don’t get this reference, you probably don’t understand this question anyway).

The second “stuff” that this could refer to is the problem of skin–to–skin contact. I mean, condoms do not cover the whole area (or, at least, they really shouldn’t). There are a couple STIs that can be transmitted through skin–to–skin conduct. This list includes a bunch of grody stuff like crabs, HPV and the herp, but these are some of the most preventable STIs. HPV inoculations are a good place to start. Both men and women can get them now! Female condoms also reduce the risk of all these diseases because they cover much more skin than regular condoms. That being said, most people do not know what a female condom is or how to use it. They can be a little awkward, but if you are freaking out about getting herpes, they are worth looking into.