West Chester Matchmakers | How to Date a Successful Woman

By Philadelphia Singles Dating Service
Home / Dating Advice / West Chester Matchmakers | How to Date a Successful Woman

There’s a new breed of women in town—they’re high-earning and successful. From CEOs to entrepreneurs, more and more women are earning more than men. And how do men feel about this? Well, many of them don’t like it too much. But why? Here at Philadelphia Singles, we know that driven, ambitious, go-getters are sexy and desirable—not to mention, they make for excellent partners.

How to Date a Successful Woman Without Feeling Like Less of a Man

If you’re one of those men who feels that having a successful girlfriend makes you less of a man, then this blog is for you. Today, our West Chester matchmakers will show you how to date a successful woman and keep your dignity intact.

single women in philadelphia

1. View Her as a Person

Having a girlfriend who earns more than you is no different than having a girlfriend who is just starting out in her career. She is more than her job or her bank account. She is a woman you’re just getting to know.

Instead of worrying about how much money she makes, ask about her hobbies and interests, what foods she likes to eat, and who her favorite football team is. We totally hope it’s the Philadelphia Eagles, but humor us. And even if she’s not a football fan, she has to support Philly after our first Super Bowl win!  Find out who she is and what makes her tick.

2. Be Honest About Your Insecurities

Instead of always looking at how successful she is, think of the real reasons you have a problem with this situation. Do you suffer from low self-esteem that’s causing you to feel insecure? If so, try to work on that so you never face these feelings of intimidation again.

You need to be honest with her. If it bothers you that she takes you to expensive restaurants and pays your way, buys you designer suits, and is always talking about money, talk to her about it, and let her know that it makes you feel uncomfortable. Honesty is the best policy in a relationship.

3. Don’t Be Intimidated by Her

Instead of looking at how much money she makes, look at her as you would any other woman. After all, she has the same needs as any other woman in a relationship. Any man who confidently loves her will treat her with respect, and that’s what you need to do.

Focus on the things you do have and what you bring to the table. Play up your strengths. Okay, so maybe you can’t take her to the most expensive restaurants in Philly every weekend, but you can, however, make her a delicious meal at home or do something else that is romantic. Believe us, those little everyday gestures will mean much more than expensive nights out on the town.

4. Don’t Look at It as a Competition

Don’t let your pride ruin this beautiful relationship. Sure, she has climbed up the career ladder and now earns more money than you. But that doesn’t mean you should work yourself to the bone to compete with her. If she buys you an expensive gift, that doesn’t mean you need to buy her an expensive gift in return. Look at her success as an inspiration, but don’t let it ruin your relationship.

Trying to keep up with her expensive lifestyle might leave you in debt or make you resent her. If she really cares about you, she won’t view you as any less.

5. Be Attractive

You don’t have to have six zeroes in your bank account to attract a successful woman. If you really want to impress her, be physically and emotionally fit. After all, she already chose you as her man, so she is into you. Being physically attractive and emotionally stable will make her drawn to you, even if you do make less than her.

Always remember that you’re dating a successful woman, not a bank account. Despite her career and success, she’s still a woman and deserves your affection and attention so it’s time to put your ego aside and appreciate her.

If you’re single and struggling to meet quality women on your own, contact our West Chester matchmakers and let us introduce you to relationship-ready single women in Philadelphia who are attractive, successful, and compatible with you.

To reserve your FREE (90-minute) matchmaking consultation, simply fill out the confidential form at the top of the page today.


Recommended Posts
Contact Us

We're not around right now. But you can send us an email and we'll get back to you, asap.