How to Date a Successful Woman

woman in red dress

According to the Catalyst, “56.8% of all women 16 years and over were in the labor force in 2016,” and “Women held 51.5% of management, professional and related positions.” These knock-outs are running multi-billion dollar companies, starting businesses of their own, and bringing home their own bacon. So has this changed the rules of the dating game? It certainly has.
A single and successful woman’s approach to life, relationships, and time is entirely different. So how do you build a strong relationship? Where should you go to meet successful women? Do you pay for dinner still? What if the woman of your dreams makes more than you?

It’s stressful to think about, but it doesn’t have to be difficult. With these dating tips provided by love experts and female entrepreneurs, if you find a business woman that captures your fancy, you’ll know exactly what to do.

A Chivalrous Act Now And Then Doesn’t Go Unnoticed

man with roses

You might think dating a powerful woman means cutting out all the traditions of courting. It’d be an insult to open the door for them, offer your coat, or pay for dinner, right? On the other hand, isn’t it still a charming gesture?

Successful women are capable of fending for themselves and don’t need your coat, but it’s still a show of kindness that won’t go unnoticed. She’s spends her days in control, getting things done and dealing with high pressure situations – perhaps in a work environment that pits her against chauvinist men who truly believe she doesn’t belong there. So it’s nice to be appreciated and taken care of once in a while, by a man who realizes liking it isn’t a show of weakness.

The key is to start out slow and work up. Ask if she’d like you to pick her up for a date or if she’d like to meet at the restaurant; don’t insist on the former. Get the door for her, but don’t bat an eye if she reaches for it first. If she offers to Dutch Treat for dinner, don’t insist that you pay.

By allowing her to circumvent these traditions if she feels like it, and by not insisting “because I’m a gentleman and that’s how it’s done,” you’re making these gestures clear as what they are: acts of kindness. Not a strict social norm because you’re a man and she’s a woman, and somehow those two genders need to be treated differently.

What If She Makes More Than You?

woman drinks wine

It can be intimidating, yes, but this can actually work to your advantage. If you were dating a woman who couldn’t afford lavish gifts and dinners, of course she’d be charmed by them. However, a woman who makes more money than you? She can buy and enjoy luxuries herself, so she doesn’t need them from you. Instead, this is a brilliant opportunity to focus on the experience, not the price tag.
Don’t feel pressured to buy her a five-star dinner. She could buy that if she wanted it, but what she can’t buy is a romantic picnic in the park, or evenings in with a home-cooked dinner and her favorite wine. Don’t buy her expensive jewelry; if you’re crafty enough, hand-make something yourself that’s special to a moment you’ve shared or something you have in common.

As the author of Becoming a Female Entrepreneur: Simple Strategies to Make It Happen, Jennifer Kelman, says, “Take the lead and play a traditional male role in the relationship in other ways, like planning dates and opening doors.”

Play It Cool, Man, Play It Cool

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Let’s face it. Dating a powerful and successful woman can be terrifying. You want to impress them, but it’s difficult to do when you feel out of your element.

That fear will leave as you come to know each other and form a strong relationship, but in the meantime – play it cool. Don’t show that you’re intimidated. Instead, compartmentalize that insecurity and focus on subjects you are experienced with. They hear work-speak at work all day long. Instead, what are their favorite books, hobbies, and movies? What do they think of your favorite music or places you’ve visited?

How to surprise a working woman nowadays? Allow her to be a respected business mogul and an attractive woman.

Be Honest When Things Move Out of Your Comfort Zone

couple on the walk

With the above two points in mind, if things venture outside of your or your bank account’s comfort zone, say that. According to Nick Savoy, author of the Magic Bullets Handbook, “If you’ve planned an evening you can’t afford just to impress her, consider making different plans.”

She wants to visit an expensive restaurant and you can’t afford it? Say so, and suggest either she covers this dinner and you’ll cover the next one or that you both eat somewhere else. There’s no shame in the differences between your bank account – and she’ll find your honesty, your confidence, and your money-wisdom appealing.

She wants you to accompany her to a party with all her colleagues? If you’d feel out of your element or are worried that you’d embarrass her, lay out your fears or worries, and make it clear you’re declining because you wouldn’t have fun, not because you don’t support her.

Have Respect for Her Dedication – and Boundaries

woman in black

A businesswoman is a busy person. The lifestyle requires extreme focus and a precise arrangement of boundaries to allow a comfortable work/life balance, and you can be sure she’s fully aware of every decision she makes. She’s designed a day-to-day schedule that helps her and her career thrive – and won’t devote attention to something which draws away from her productivity. This is especially true with dating and careers.

If she’s making space for you, this is because she thinks you’re something special – and worthy that time. Take comfort in that. She didn’t start dating you on a whim; she truly values you, because if she didn’t, she would have decided that when plotting out where to fit you into her life.

But be careful that you don’t challenge these boundaries. If she says she’ll be booked all week, don’t pressure her to cancel or rearrange commitments in order to spend time with you – even if it’s a holiday. If she has to spend her lunch break or time after work catching up on to-do lists, respect her texting and calling radio-silence. You can be certain she’s already weighed the pros and cons, as well as the implications, of that decision. You won’t change her mind; you’ll only make yourself an additional source of stress. Or if you do convince her, she’ll be compromising her carefully-arranged lifestyle for you. Making a successful woman choose between ‘love’ or ‘career’ can only lead to trouble.

Make Time for Each Other

woman on the walk

The above point in mind, that doesn’t mean you should leave your time together entirely in limbo – or worse, sacrifice your time for hers. Schedules will conflict and there may come moments where you hardly see each other for a week (or three), but it’s important to ensure you both have a place in each other’s life. Be willing to bend your schedule a little for her, and she’ll be able to bend it in return.
Most importantly, try to have a set day for each other – especially as the relationship becomes more serious. For example, every other Saturday is your date night. You may go out to dinner every Saturday, or spend time together for a quick drink or lunch dinner throughout the week – but if schedules become hectic, you can always be certain there’s a slot biweekly that’s just for the two of you.

Show Interest in Her Career

woman drinks red wine

A successful woman doesn’t reach a position like hers without being invested in her career. It matters and is a part of her, and showing interest will not only help you better understand her – but also make her feel valued. No need to become an expert or offer advice about her job (definitely not that, because she’s certainly used to pushy men trying to tell her how to do her job), but showing genuine curiosity about her career indicates genuine respect. The longer you’re together, the more important this becomes.

Pro-Tip: Do the “If She Was a Bro” Double-Check

woman walks

Your first thought is what you’re conditioned to think; your second thought is what you really think. It’s okay to have a vaguely misogynist brainwave now and then, so long as you reel it back and get yourself in check. It can be difficult shaking off the social norms – even if they’re outdated – and you may revert to them by accident.
To make sure you’re not doing her a disservice – discounting what she does or the level of encouragement you offer her – every so often, stop and run this scenario through your head: If she was a bro… and she canceled dinner to work late, would you be upset or would you respond with “no problem, man, do what you gotta do”? If she was a bro… would you congratulate her and praise her talents after gaining a huge promotion, or would you leave it at “good for you”? If she was a bro… would you find her increasing success threatening or shake it off?

In that same vein, if she was a bro… would you go over the top praising her work? That can be insincere and lead to just as many problems. Be yourself, and if your friends find that awesome about you, if she’s the right person for you, she will too. Just make sure you’re offering her the same level of respect you offer others.
Give it a try. Using this double-check strategy often enough will eventually make it your new default. Your reactions will be fairer and she will find this devastatingly refreshing.

Dating a successful woman can be a daunting task – but when broken down, is actually rather simple. At the heart of it, they want to be respected and still be treated as an eligible, attractive woman.