People You Shouldn’t Date

Getting involved with these people is more likely to result in heartache than happiness.

It’s a fact of love. There are certain people you just shouldn’t date. Of course, they’re often the very people you find yourself wanting to date.

Now, this isn’t to say these relationships can never work out. I’m sure many people can come up with an example of each of these relationships that turned out just tickety-boo.
But that doesn’t make me wrong. Getting involved with these people is more likely to result in heartache than happiness.

Your Employee

The reasons for not dating your employee are similar to those for not dating your boss, just in reverse. Your colleagues will question your judgement and your other underlings could resent you. Lover’s spats will create office tension and the power dynamic (mentioned before) can rock you out of your position of authority. Things can get ugly if you need to lay off or fire your lover. Not to mention, there’s a good chance you might get fired yourself.

Your Therapist

Oh, what a cliché! Your therapist really listens, he/she understands you better than anyone else, you can really open up! Yeah. That’s a therapist’s job. You should question the moral integrity of any doctor who would violate professional ethics by getting romantically involved with a patient. Your vulnerability makes the action a predatory one. You’ve likely told this person things you’ve never told anyone and this means they know too much.

Someone Else’s Husband/Wife

Obvious. Right? Then why do so many people get caught up in extramarital affairs? Nothing good can come of being the other woman/man. You’re part of a deception, you’re hurting someone and you’re enabling your ‘partner´ to be an irresponsible, self centred liar. Cheating is childish and cruel and you will only wind up getting hurt in the long run. Some people waste years of their lives in such relationships, only to wake up one day and realize the opportunity for true love and a family may have passed them by. Don’t do it to yourself.

Your Friend’s Ex

Unless your friend is really cool, even if they say it’s OK, it’s not. They’re lying. Dating a friend’s ex can cause a world of hurt. Even if your friend is the one who initiated the break up, there can be residual feelings of romance and resentment. It will pain your friend to see you together and, if you decide to try to avoid that situation, you’ll have to make sure you’re never all in the same place at the same time, which can be a nightmare. Also, you might find yourself worrying that there’s still a spark between the two. And you might be right.

Your Own Ex

OK, I flip flopped about putting this one in but came down on the side of inclusion. Here’s why: you broke up. And even if there’s love and affection, there’s also bad blood. Resentments, in most cases, will eventually bubble to the surface and boil over and you’ll be right back where you started – apart and hating each other. Because remember that annoying thing they did that used to drive you CRAZY? They still do it.

John Mayer (Just for Laughs)

Yeah, he’s kind of cute and he says your body is a wonderland. But he’s a(n alleged) womanizing heartbreaker! And we use John here to represent all womanizing heartbreakers. Stay away. Also, he blabs about his love life to the press. Jessica Simpson was apparently none to impressed when he referred to her as ‘sexual napalm’ in an interview (though some might see that as positive publicity). Rumour is that Taylor Swift’s song ‘Dear John’ is about her romance with Mayer. Oh, for that matter, don’t date Taylor Swift, unless you want to wind up the subject of one of her songs.

Know of any other obvious bad people to date? Send your comments to Gossip Guy at or comment in the comment box below to give your insight.

Gossip Guy, you know you love me -xoxo


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