5 Tips for Dating a Successful Woman

Dating a successful woman may seem intimidating, but following these golden rules will help you transform into a more attractive suitor for any romantic interest.
By aha insurance - Feb 13, 2020

At aha insurance we continually explore ways to stay in control of all aspects of life – because we know life is about more than insurance. In our Life Matters series we talk about staying in control of your life and living on your terms. Control feels great!

Now more than ever, successful women are all around us, crushing it in their careers and personal lives. Attracting and keeping her interest shouldn’t be about flashy first impressions or spending money you don’t have on expensive merchandise.

If you can embody these 5 effective tips for dating a successful woman, you’ll be well on your way to making your love life as successful as the strong woman you want to build a relationship with.

1. Work on feeling secure with yourself and let her inspire you towards self improvement.

Working on your own insecurities is crucial for the success of any relationship, regardless of which one of you is more successful on paper. If you’re resentful of your partner’s success, it’s a sign that you’re insecure and need to work on building your self-confidence. Successful women are naturally drawn to confident people.

The good news is that if she makes more money than you and she’s still interested, then she likes you for you, not your bank account. Return the favour by not comparing paychecks. Instead, be a person she can count on for the emotional support and stability that’s so important to a healthy relationship.

It’s not usually a good sign when a romantic partner wants to mould you into a person you’re not, but It’s okay to let a successful woman inspire you towards bettering yourself.

  • If you admire her style, you don’t need to wait for her to buy you designer duds to raise your fashion game.
  • Do you admire her financial success? Level up on your wealth management knowledge. Even if you don’t have much “wealth” to manage, it’s never too late to start investing in your financial future.
  • Admire her passion for her career? Maybe it’s time to start carving a new career path out for yourself or to seek new skill building opportunities?

Investing in self-development is the best way to avoid being intimidated by your date. Why would you want to be intimidated by an amazing woman when you could be in a fulfilling relationship with one instead?


2. Listen and hold back on offering unsolicited advice.

Everyone appreciates being heard, and successful women will often have more stress on their plate and fewer people to vent to than the average person. If she’s meeting you for drinks after a hard day at the office, she’ll probably appreciate having the opportunity to talk out some of her frustrations with an empathetic listener.

By all means, offer her your opinion and advice if she asks (she needs an engaging conversation partner, after all), but avoid harsh judgements or trying to explain what she should have done in any given situation. Nobody wants to have to defend themselves from an overly critical partner, so save the good-natured debates for a topic that’s more fun and less personal.

3. Treat her to something special.

An independent woman doesn’t necessarily need or want you to pick up the tab every time you go out. As a modern woman, she likely enjoys treating you just as much as you enjoy treating her. This makes it all the more important that you put in the effort to listen to her interests and treat her to gifts or experiences that she’ll find particularly meaningful.

Don’t buy her something just because it’s expensive. Maybe she’d prefer something more modest and thoughtful, like tickets to see her favourite band, a play, or a sporting event—with the added pleasure of your company of course. Something as small as a beverage made just the way she likes it from her favourite coffee shop could be the perfect treat to brighten up her stressful day at work.

4. Don’t be afraid to take initiative.

Healthy relationships involve a relatively equal distribution of effort and participation from both parties. By definition, successful women are intelligent go-getters who are comfortable with planning and decision making, but you shouldn’t expect her to do all the work for your date nights. Ask for her preferences:

  • Friday or Saturday evening?
  • Italian or Thai food?
  • Romantic comedy or indie film?

Then you can take the reins and plan a romantic evening that she’ll enjoy even more knowing you took the initiative to plan something special with her in mind. She might be known for being great at organizing her social calendar, but even the most successful among us need some time to sit back, relax, and enjoy being treated.

5. Give her the courtesy, respect and support she deserves.

Every woman you date deserves respect regardless of how much money and status she’s bringing to the table. Successful women know their worth and won’t let someone who doesn’t take up their precious time and emotional bandwidth.

Manners are always paramount, but in the modern age of digital dating it’s more important than ever to stay present on a date. When the two of you are face to face, avoid looking at your phone at all costs unless there’s an emergency, or she really wants you to Google the name of that actor who was in that movie you’re discussing.

Some successful women will also appreciate the directness of a phone call rather than a text to ask her out. Just make sure you don’t call her at a time when she’s likely to be busy with work or one of her other many responsibilities. Responding to her attempts to reach you in a timely manner is also important.

Speaking of time, it’s crucial that you’re extremely respectful of each other’s time. Don’t expect her to rearrange her schedule to meet at a place and time that’s only convenient for you, or to spend the night at your place when she has work in the morning. A successful woman knows how important her time is, so she’s likely to return the favour and respect yours as well. Do your best to show up to every rendezvous on time and well put together. You don’t have to be a trend-setting millionaire to show up for every date well-groomed and wearing the appropriate attire to show you care.

Lastly, and most importantly: be supportive of her achievements. Unfortunately, high-achieving women can face a lot of negativity and criticism from their peers. Show that you care about her success because you care about her. Just because she can pay her own bills doesn’t mean she doesn’t need awesome people like you routing for her as she works her way to the top. Comfort her during setbacks and help celebrate her wins, because when you’re in a successful relationship with a successful woman: Her wins are your wins too!

These 5 effective tips for dating a successful woman boil down to essential pillars every relationship needs to build upon. Take care of yourself and build your confidence so that you can show up as the best version of yourself for the successful woman in your life. Put in the effort to treat her right, and if you’re right for each other—a successful, long-lasting relationship could be in your future.

aha insurance is Canada’s first car and home insurance brokerage to offer a fully online customer experience. Customers can purchase and manage their car and home insurance online in minutes from the convenience of wherever they are. This puts customers in complete control, and control feels great.