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The Successful Woman’s Guide To Dating

by eHarmony Staff

The Successful Woman's Guide To Dating

Ladies, let’s face it — dating in the modern world can be tricky. Between work, play time with friends, and managing everyday life, not to mention online dating, and the occasional fun flirt fest with a random cutie you actually meet in person, the chances of finding someone really special to connect with and date long term can feel increasingly more challenging. And if you happen to be a super successful female who makes more than most single men she meets? Well, that can sometimes make your chances of success seem even tougher.

While you should never have to apologize for having a career and making great money, the reality is that at some point in your dating life you may encounter a great guy who’s intimidated by your success. Rather than throw your hands up in disgust and give up on dating altogether, the following five tips should help you handle the sometimes sensitive subject matter with your potential dates:

Tip #1: Be clear about what you want

Just as the key to succeeding in business lies in setting goals, working hard, and overcoming setbacks along the way, the key to succeeding in the dating world is to be equally clear about what you want and then go for it.  As a successful woman, it’s probably even more important to be clear about the type of guy you’re looking to attract because chances are you’re short on free time. First, make a list of the top five qualities you’re looking for in a potential partner.  While money doesn’t have to make the list, you should next ask yourself this: Does equal or greater earning power matter to you? Do potential partners have to keep up with you financially or would you be willing to date someone who makes less than you, but is fabulous in so many other ways?  Only you will know the answers for sure, but it’s absolutely essential that you determine the top five qualities you’re looking for in a potential dating partner so that when you’re out and about, you’re clear about what you want and cut down on wasted time (both yours and potential dates).

Tip #2: Create (and maintain) realistic expectations

In a time when successful women can buy their own homes, take fantastic vacations, and still have enough money to shop, invest in their 401(k), and enjoy midweek cocktails with the girls, it may come as no surprise that successful single women have high dating expectations.  And while having high standards is important, having unrealistic expectations will keep you single.  Case in point: Just because the rest of your life seems pretty perfect doesn’t mean that an imperfect guy can’t fit into the picture.  Whether he makes less than you, drives a more modest car than you, or has significantly fewer assets than you is irrelevant.  What’s important is who he is as an individual.  Again, review your list of the top five qualities you’re looking for.  If he makes you laugh, lavishes you with affection and kindness, shares a similar life vision to yours, these are the potential qualities that can make a man a fantastic and possibly lifelong partner. 

Tip #3: Get to know your date (and let him get to know you!)

A first date should be just that — an opportunity for two people to get to know one another as individuals.  It’s not a time to exchange financial statements, career accomplishments, resume highlights, etc. As a successful single woman, use this traditional dating etiquette to your advantage.  Let the person you’re on a date with get to know the woman behind all the success — the real you!  And while you shouldn’t hide or apologize for your success, you can reveal it in a comfortable, relaxed fashion as you get to know someone over the course of several dates. If, for example, you’ve had bad experiences with men who couldn’t handle your success, do your current to date a favor and DO NOT carry that baggage around with you.  Not every guy is like that. By being comfortable with your own success, your date is all the more likely to be comfortable with it, too. So just sit back, relax, and be your fabulous self.

Tip #4: Give your date opportunities to woo you

As a successful single woman, you would be doing yourself a disservice to deny the fact that men traditionally take pride in being the bigger breadwinner.  Does that mean you’re screwed when it comes to dating?  No.  But it is important to understand the psychology that’s at work.  Many men feel validated by their career success.  Dating a woman who makes more than they do and/or enjoys greater career success may initially threaten their sense of self worth. They can quickly rebound and find other ways to feel validated and worthy, but they may need your help.  For example, until you know his level of emotional maturity, don’t take him to expensive restaurants and offer to pick up the tab, and don’t buy him expensive gifts.  Let him pursue you, give you gifts, plan outings, and pay for things. Show your appreciation of his efforts regardless of how big or small they are.  These gestures are relatively minor, but they have major results in making him feel validated and appreciated.

Tip #5: Always make time for the guy in your life

Oftentimes, men who date successful women report that they feel like they come in second to the woman’s career. And while you shouldn’t have to compromise your career ambition for the person you’re dating, you should always make time for them.  For example, on a romantic dinner date, don’t constantly check your Blackberry.  If possible, leave work completely out of your time together.  If that’s not possible, let your date know that you may have to attend to work occasionally in your shared free time, but that they’re still a priority, too.

So there you have it — five tips for how to navigate the dating scene as a successful single woman.  Ultimately, the right guy will not be intimidated by your success.  In fact, he’ll help you celebrate it!  But in the meantime, use the tips above as needed.  Good luck and happy dating!

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