How to Date Successful Women and Not Feel Like Less of a Man

how to date successful women

Traditionally, men were the breadwinners. Increasingly, women are bringing home the dough. Here, we show you all the ways to date successful women.

A new breed of woman—the high-earning, successful woman—is on the rise. From company CEOs to business moguls, more and more successful women today are out-earning men.

And how do men feel about this? Many confess they feel emasculated. As their female partners, who society and tradition have long dictated belong in the house and with the kids instead of behind desks, are now wearing the pants in the relationship, as the breadwinner.

How to date high-powered and successful women without feeling small

If you are one of those men who feel having a girlfriend more successful than you is a blow to your ego, you’d better read up on these tips to help you deal with dating successful women.

#1 See her as a person and not a title or bank account. Having a girlfriend more successful in her career than you are in yours is no different than having a girlfriend who is not as successful or is just starting out in her career. Especially in the first few months of your relationship, get to know her as she is. She is so much more than her job or her bank account.

Instead of focusing on those things, delve deeper into what she likes, the music she listens to, the food she loves to eat, her favorite basketball team. Basically, all her interests. You may be surprised to find you have much more common ground and goals than you thought.

From here, you gain a better grasp of what you can do together, instead of worrying about your career differences. [Read: How to get to know a girl: 17 ways to win her heart]

#2 Be honest about your insecurities. Instead of always looking at how successful and intimidating she is, think of the real reason why it is such an issue to you. Do you have low self-esteem, and that’s why you get easily insecure? It helps to be honest with yourself about these things, so you can work them out.

Likewise, be honest with her. If it bothers you that she takes you to expensive fundraising galas, pays for you, and gets you designer suits, then talk to her about how her actions make you feel. Things that make you uncomfortable must be addressed, especially when you are starting out in your relationship.

#3 Don’t be intimidated by her. Instead of looking at her and how she stacks up against you, look at her just as you would any other women. After all, she has the same needs in a relationship. A guy who confidently loves her and treats her right.

Focus on what you have and what you bring to the table. Play up your strengths. If you cannot give her expensive gifts, at least cook her dinner or teach her how to do something you’re good at. [Read: How to be a better boyfriend: The best she’s ever had]

#4 Don’t look at it as competition. Don’t let your pride and ego get in the way of your relationship. Sure, she earns more or climbed up the career ladder faster and higher than you. That doesn’t mean you should work your ass off, take no days off, and compete with her. Or, if she buys you a Rolex, that doesn’t mean you sell your place just so you can give her a Birkin. Look at her success as your inspiration, but don’t let it get to your head.

Trying to keep up with her lifestyle might have you in debt and with a lot of resentment toward her. If she really cares a lot about the brand of your clothes, the car you drive, and the vacation spots you go, then rethink your own priorities against the role she plays in your life.

After all, the right woman for you wants someone who she celebrates her successes with, instead of having to defend or downplay them to avoid hurting your ego. [Read: How to date a girl who seems way out of your league]

#5 Be fiscally fit. You may not have the additional zeroes to your bank account, but at least you’re not driving yourself to being dirt poor with the way you spend. If you see her tip the valet a hundred dollars, don’t ever feel that you can do the same with what you’re earning. If you really want to be in the same league as her, then start with very small steps and make financially sound decisions right now.

Instead of wanting to buy designer things for yourself, just because your girlfriend wears designer from head to toe, keep that money in the bank—or, better yet, invest it. After all, the right kind of woman will not be interested in how much you make, but your ability to spend within your means, saving for the future, and still having the best time together. [Read: 20 ways your over-analyzing is ruining your relationship]

#6 Have fun together. Just because she’s the boss of her own firm, or she goes to different countries on business trips, doesn’t mean she doesn’t want you to be a big part of her life. You notice how important you are to her if she carves time out of her chaotic schedule to see you.

Although making your schedules meet can be challenging at times, learn to compromise with each other and make the most of the time you have together, even if it means staying home.

#7 Be more creative with gifts. Chances are, whatever you think you’re going to give her, she already has. So, instead of giving her expensive gifts that break your bank, make room for creativity and thoughtfulness when it comes to showering her with gifts.

Write her a song, compose a tune, create pottery, plant her a garden, cook her food, or simply be her handyman. She loves these little gestures not because they are extravagant, but because you took extra time and effort to please her. Likewise, plan outings to someplace she’s never been to. It doesn’t have to be some luxury destination, but the fact you put more thought into taking her someplace you know she will like is enough to light her up. [Read: 20 unique ways to make your girlfriend incredibly happy]

#8 Still be the man. So, she’s raking in large amounts of money and takes you on expensive dates—don’t be a baby or a burden to her. Treat her just like you would any woman *unless you’re really a selfish, self-absorbed jerk* and take the lead in your relationship. Plan your dates, open doors for her, lead her to her seat, and continue to be the gentleman that you are. Continue to be the decision-maker in the relationship, but don’t go to extremes just because you are nursing your hurt ego.

On the other hand, if she continues to act like the boss outside of the office and in your relationship, you should think twice and determine if that is what you really want in a woman. [Read: What to do when your partner earns a lot more money than you]

#9 Split the bill. While splitting the bill is looked down upon by many dating traditionalists, and she may not like it during the first few dates, it can be fine to consider later on in your relationship. This is especially true when you move in together or cohabitate.

You each must contribute your share on an equal percentage of your income. Furthermore, if she wants an activity out of your budget, be honest enough to tell her about it. You never know—she might understand the situation and swap it out with a more cost-friendly activity. If she offers to treat you or pay for her share, accept it graciously. [Read: 12 really sweet ways to tell a girl you love her]

#10 It’s okay if she pays. Instead of looking at dating a successful woman as a blow to your self-esteem, look at the perks it gives your pocket. In letting her pay sometimes, you don’t have to bear the full brunt of dating her.

Sit back and enjoy the moment, marveling that you are dating an amazing and successful woman, while still having enough cash left for yourself. You’re not only saving a portion of your dating cash—you also take home someone with beauty and brains, and a lot of determination and ambition.

[Read: 15 highs and lows of dating someone smarter than you]

Always keep in mind that you are dating a woman, not a job title or a bank account. Despite her career success, she is still worth your time, attention, and affection. It’s now up to you to put your ego aside and appreciate that this beautiful and successful woman drives you to be at your best, too.

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Tiffany Reyes
Tiffany Grace Reyes
Tiffany is a wordsmith who has played with words ever since her letter-to-the-editor was published nationally at the age of 9. Since then her writing has gone f...
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