» Can you Date these People and Live to Tell About it?

The boss. The neighbor. The brother of a friend. Is it worth it to date these people given that the relationship may not work out?

Dating people whom you see every day may seem convenient, but if and when your relationship starts to fall apart, what happens to the wreckage that’s left behind? We’ve compiled a list of people in your life who may seem to be good dating choices but end up testing your gumption when the relationship falls apart.

1) The Coworker

Considering that we spend more time at work than anywhere else, it’s no wonder that people wind up dating their coworkers. Being in close quarters for the better part of the day gives love ample chance to bloom.

The major pro of this situation is that that you have so much in common. The two of you commiserate over the boss, brainstorm over a pending project or talk about upcoming changes in your department without fear of boring each other.

The cons? You’ll see this person every single day, which is likely to cause your relationship to fizzle fast. Also, consider that your love affair will not be received well in your office. Once you “come out” or are “found out,” your colleagues will feel the difference. They’ll take notes when they sense your productivity is lacking or when the two of you are giggling alone in the lunchroom.

Final analysis: While dating someone at the office may seem like a resourceful way to be excited about work, you’re taking a big risk. If you and your flame are exceptionally mature, give it a whirl. But tread lightly and be aware of the “pink slip” consequences or the fact that you may need to transfer to Toledo should things go awry. Finally, if you are set on an office romance, you should tell Human Resources about it right away. Most companies have rules about interoffice dating, and you’ll want to make sure you’re adhering to them.

2) The Boss

It’s flattering when the guy or gal who’s running the show wants to be involved with you. Conversely, attraction to a person in power is understandable. And also, for those looking to get ahead, dating the boss seems to be a perfect way to skip a few rungs on the corporate ladder.

Here’s the flip side: No matter how nice you are or what kind of work you produce, your coworkers will resent you and gossip. If and when the relationship dies, it’s very possible that you’ll lose both your new love and your job.

Final Analysis: Dating a person who is in a superior position to you professionally is a bad idea. Starting a romantic relationship with an authority figure mucks up the lines of communication and respect, making you exempt from the traditional rules that protect you.

3) The Neighbor

While you’re out mowing the lawn or washing the car, it’s natural to catch up with bordering buddy Mr. Rogers on a Sunday afternoon. Pretty soon you two are pretty chummy, stopping over for lunch instead of the occasional bowl of sugar or stick of butter.

Dating the neighbor is definitely geographically desirable because there’s practically no commuting involved. However, should your relationship fall apart, remember that you will run into your old flame frequently. Not only will you see this person out in the yard or pulling into the driveway, but also at the grocery store, cleaners, gas station and so on. Further, you may be privy to the person’s business after you are long gone.

Final Analysis: If your romance goes south, it may be uncomfortable to see your old neighborly flame around town. With time, however, the anxiety of seeing your ex and pangs of regret will wane. But if you really love where you live and know you can’t handle the aftermath, don’t risk it.

4) A Friend’s Sibling

Dating a friend’s sibling always has its pros and cons. To your advantage, you can get the full scoop on what type of guy or gal your partner is, what the person dressed up as for Halloween at age 6, and how the person gets along with his or her family.

If you choose to get involved with a friend’s family member, know that your relationship between you and your friend will change. No longer will the friend be your confidant, the person you run to with your relationship problems. Also, once the romantic relationship fizzles, you may lose your significant other and a friend, as many people operate under the credo that blood is thicker than water.

Final Analysis: If you must date a friend’s sibling, keep your pal out of all operations as much as possible. It’s quite possible that your friendship may never be the same, as loyalty generally sways to family. So proceed with caution and carefully weigh the consequences.

5) Your Ex or Your Friend’s Ex

It’s called a breakup because the relationship is broken. Revisiting a previous partnership with expectations of a sudden dramatic change in your ex is futile. Although second chances may be gracious, or even deserved, it is not guaranteed to work. Actually, it probably won’t.

And if you are eyeballing your friend’s ex-guy or ex-gal, you’re in for trouble. That person dropped the ex for a reason, so take notice of the motives that lie before you. Not to mention that you will look like a total jerk taking your amigo’s seconds, looking less like a friend and more like a foe.

Final Analysis: Don’t be a fool, and retire the sleeping dogs. Revisiting an old relationship seldom works, and it often leaves you reeling with regret. On the rare occasion that a friend’s ex is recommended or even encouraged, then you may be in the clear. But take into account that you may be trading in a great friendship for a big heartbreak.