Dating Great! with advice by

Ask April: Dating Your Boss

"Ask April" Author of the best selling, "Date Out Of Your League"
Read chapters from April Masini's books here

Q: Dear April,
I think I’m in love – with my boss! He’s not married, and he’s not too old for me, but somehow, I feel like I’m doing something wrong. Am I? Signed, Working It

A: Dear Working It:

Of course you fell in love with your boss. You’re probably like every other workingwoman who is dedicated and hard working – so much so that her commitment to work makes it impossible to meet anyone outside of work. You’re probably not just a nine to five worker – you’re that successful someone who works extra hours, weekends, and is trying to get ahead and do well. You know what that makes you? Sexy!

Men love women who are confident and focused with interests and areas of expertise. Who wouldn’t? Think about it. It goes both ways. Women love men who are like that, too – and what simpler place to meet them than at work?

However, that doesn’t mean you have to go through with it. The easiest way to get out of dating someone at work is to simply explain, “Sorry. I don’t date people I work with.” Then hope one of you gets fired.

Here are some considerations in deciding if dating someone at work is right for you:

Pros and Cons of Dating A Co-Worker

1. You know he or she has a job. You know how he or she is thought of at work.

2. You have a lot in common and can be more productive because you have this in common.

3. There is an understanding of each other's work schedules. One of you isn't angry if the other has to work late because you have a better understanding of what's involved.


1. If you break up or have a fight, you don't get the respite and space you may need to heal or cool down because you'll see the person so often at work.

2. Sexual harassment is a real problem that can occur more easily when there are lines that get blurred at work. In addition, people gossip and you may make enemies if one of you is higher up in the corporate or business ladder at work, and the one is lower down may be perceived as getting unfair advantages.

3. If one of you wants a break from work and the other is into work, you may not have an escape from it -- even out of the office.

Date at Work – But Work at Dating
Okay, so you’ve thought about it, and you’re still with me that dating someone from work is viable and can even be successful.

Even though it’s often advised against, dating people you work with makes practical sense—after all, we spend so much of our lives in the office, there’s often no other way or time to meet anyone else. But that’s not to say you don’t have to be smart —extra smart, in fact—about your choices, and take special precautions if you’re going to venture into an office romance.

Water Cooler Gossip
The one overriding warning worth heeding—the one that should dictate all of your actions and words—is this: People talk. No matter how friendly your co-workers are, or how tight-lipped the object of your affection seems, secrets are almost always spilled, one way or another, whether accidentally or intentionally. Translation? Say nothing and do nothing that you do not want everyone else to know about. This means no chit-chat with the girls at the water cooler about his size or performance, and no pillow talk with him about how much you loathe your boss, and can’t wait to take over his or her job. There’s too much at stake—like, your livelihood—to take risks, and there’s too much to lose—like a potentially great love—not to give it a shot.

Rules About Dating Co-Workers
1. Don’t mix business and pleasure on company time. Agree to date out of work hours, but don’t turn a business lunch into a romantic lunch.

2. Stay fair. Don’t give someone you’re dating better work or pay, and don’t punish someone you’re breaking up with by giving him or her worse work or pay. Otherwise, you may find yourself on the receiving end of a lawsuit!

3. Make sure he or she is actually single. If they’re not – then keep personal remarks at work limited to sports, the weather and the kids. Don’t gripe or listen to gripes about a spouse. “I’m sorry, I’m not comfortable talking about your wife – I want to keep our relationship all business because I value us as co-workers,” is all you need to say – and do.

Dating Your Boss
Dating your boss may be a lightning rod for trouble, but the truth is it's natural to fall in love with someone you work with, that you admire. And if you’re a terrific asset to the company, you’re going to catch your boss’s attention with your work. If you’re attractive, and there’s chemistry between the two of you, it’s natural for a relationship to become possible. Therefore, dating the boss is something that is taboo only if you let it be. That said, there are definitely 'Do's & Don'ts' to follow that will make or break your romance.

Do’s and Don’ts For Dating Your Boss
1. Don't Boast. Your boss may look like Brad Pitt or Angelina Jolie, and you may be so pumped up that you've got a hot date with hottie -- but keep your feelings to yourself -- and your friends outside of work. This is a great time to start practicing certain boundaries. Work gossip is inevitable. Practice good behavior by keeping the water cooler talk to work and the weather.

2. Don't Make Out or Have Sex At Work. Sorry to burst your bubble if you've got fantasies of locking the board room door and doing it on the conference table while the staff waits impatiently for the janitor to jimmy the lock open. Keep all sex and affection outside of office parameters. It's okay to meet at the office, but don't smooch at the office.

3. Don't Have Love Spats At Work. If the sex wasn't great the night before, don't bring your disappointment to your staff meetings -- no pun intended. You will have to practice wearing two hats -- even if you're mad at the boss you're dating, don't put the kabosh on his comments at the Monday morning meeting and act out your frustrations at work.

4. Do Put Rumors To Rest. If you hear gossip, don't fuel the fire by denying the truth. Everyone finds out that you're dating eventually. While you should not announce your relationship, you can say, "Yes, we're dating. We're both single adults and we were lucky enough to have found each other! We're working very hard to keep our social life separate from our work life." And smile.

5. Do Communicate Well. Dating your boss seriously, is a lot like blending families because there are so many people involved -- whether you like it or not -- and they're all wondering how your relationship is going to affect them. Put yourself in your co-workers shoes, and talk openly and often with your honey about what you see, feel and want to do about it.

Remember that both dating and working are natural parts of life, and it’s completely natural to become attracted to people you work with. If you’re both single and available, go for it! But be impeccable with your behavior and your work. You’re going to be under more scrutiny in this relationship than you would be if you were dating someone you didn’t work with.


Ready for even more bold, brutally honest, and always helpful dating advice? Visit my Web site, www.Ask There, you'll find informative articles, expert columnists, interactive quizzes, and free giveaways! And don't forget to also check out my workshops, designed to help you find you real "soul mate"!

Date Out of Your League - For The Man Who Is Ready To Date The Woman He Wants - Not The One He Settles For!

Ask April "Date Out Of Your League"

© 2005 April Masini

April Masini is a recognized and award winning producer, author, columnist, motivational speaker, relationship and success expert—with politically incorrect twist. Sure to raise eyebrows, generate buzz … and INSPIRE RESULTS!

Standing 5 feet, 8 inches tall, with a lean 127-pound body, and 38-26-36 proportions, it's not hard to understand why April Masini's impressive list of accomplishments is not the first thing that pops into a guy's mind upon meeting her. But April is much more than a blonde bombshell.
Though she started off her career as a model and actress, April has moved on to become a persuasive public speaker and President/CEO of Masini Television & Film Enterprises, LLC in Honolulu, and Masini Enterprises, Inc. in Los Angeles.

On January 26, 2004, April's no-holds-barred advice book, "Date Out of Your League" hit the stands, causing controversy with her witty, well-endowed, naughty alter-ego, High Voltage Blonde, her brutally honest, uncensored advice, and her sometimes politically incorrect message.... But controversy quickly turned into interest, and then followings, when the most widely read newspapers, magazines, and Web sites, around the world, began seeking out April's comments, opinions, and expertise.

In fact, April became so popular that in February, 2004, "Ask April" was launched simultaneously on two of FORBES Magazine's "Best on the Web" winners,, who not only won with FORBES in 2003, but was also singled out by the WALL STREET JOURNAL; along with aLoveLinksPlus, who took FORBES top award in 2001 and 2002. Then "Ask April" jumped the Pacific with the hugely popular Japanese site devoted to romance techniques.

When April isn’t writing, this former model/actress is leading seminars, guest lecturing, or dedicating her time to Masini Enterprises—her multifaceted television and film production company whose accomplishments have been recognized, record-breaking, and award winning, with strong connections to everything from "Baywatch" and "Blue Crush" to "LifeStyles of the Rich & Famous" and "The Miss Universe Pageant."




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