10 relationships that are doomed to fail

The Workaholic

He eats, sleeps, breathes his job. You believe he's simply a dedicated surgeon, a gung-ho deliveryman, a brilliant salesman. You admire his work ethic and actually feel embarrassed at your own comparative sloth. But it's not the same as working hard; a workaholic concentrates on being busy, rather than being productive. Bottom line: Career issues distract him from relationships, outside interests, even health concerns. Better to concentrate on your own career, rather than trying to compete with his.

The Addict

Nowadays, addicts come in all flavors: alcoholic, drug addict, sex addict, gambler, compulsive eater and so on. Even caffeine, smart phones and Facebook are addictive, though not necessarily deal breakers. But falling for an addict? Ultimately, he can't be there for you. You didn't cause or worsen his addiction, and your love can't save him. Get thee to Al-Anon (or a similar support group) and learn to compassionately disengage.

The Adrenaline Junkie

He's a globe-trotting special envoy for the UN, or he's an award-winning war-zone photojournalist. He was the first man to climb the Eiffel Tower—upside down. Being with him is a continual high. Unfortunately, the realities of everyday life—responding to your emails, taking you to dinner—don't interest him. You want someone who believes that falling—and staying—in love is the greatest adventure of all.

The Former Flame

Forget the 20-year reunion. Facebook makes it all too easy to reconnect with your high school sweetheart. He's single, you're single. He still has most of his hair. You like hair. But before you rekindle the romance, Nancy Kalish, Ph.D., a relationship expert at Psychology Today, asks, "How much of the lost love longing is for the person and how much is for the places of happy memories?" Only memories?! You've still got dreams for the future. Get going, and make them come true.

The Therapist

He asks questions and seems genuinely interested. He listens to you. He understands you. How can you not find him irresistible? You wouldn't be the first person to cross the patient-doctor barrier: Sigmund Freud and Carl Jung allegedly had dalliances with über patient Sabina Spielrein. But in modern times, acting on that attraction might not be just foolish, but illegal. Laws differ from state to state and professional guidelines may not be criminally enforceable, but fines can be levied and licenses revoked. And we all know about transference. It's best to stick with the fantasy on this one.

The Nearly Divorced

He's smart, interesting and separated. But he seems to be physically and emotionally available—except on evenings and weekends. You don't have his home phone number. Finally, you ask if his wife knows he's separated. The loooong silence. The sheepish grin. We call that "married."

Or maybe he really is separated. Maybe he moved out and bought new furniture and is eager to start over. Still, he's not divorced until he's divorced. And even then, he's often not ready for an intimate relationship. You might be the rebound, you might not. Do you really want to take that chance?

The Married Co-Worker

We spend about a third of our life at work. No wonder we might fall for someone at the office. However, not only is the supervisor/subordinate thing taboo—colleagues should think twice about getting involved. And he's married, too? Run for the hills—or for HR. Go down that wayward path and one or both of you could lose your job, depending on company policy. Even rumors of an office affair can threaten career advancement.

The Inmate

Not dating an inmate may seem like a no-brainer, but at least a few serial killers have married adoring fans during their incarceration—which makes the idea of dating anyone convicted of armed robber or aggravated assault seem downright wholesome. In some ways, the Inmate's the perfect boyfriend: You always know where he is, and he can't leave you. There are online groups for women who love prisoners, like PrisonTalk, and even a dating site, InmatesForYou. Sure, we understand if the father of your children spends some time in jail. But a first date in a prison visiting room?