High Performance

9 Dating Struggles Every BossBabe Can Relate To

BY Marisa Donnelly

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When you’re an ambitious woman, dating can be a struggle.

For starters, you come from a different mindset. You’re not interested in playing games, not interested in wasting your time, and definitely not interested in stringing someone along (or being strung along!) just to part ways.

At the end of the day, you only want to get to know someone for one of two reasons: because you see a future with him/her, or because you’re on the same page and just having fun.

Otherwise why would you bother with what feels like a distraction from your work?

Dating has often been on the backburner in your life, unapologetically. You don’t have time to waste with someone who doesn’t understand you. You have things to do!

Whether you’re a business owner, CEO, entrepreneur, or some other hardworking woman, you know better than anyone that sometimes relationships can be tough because you’re not willing to put aside your career for anyone else. (And that’s okay.)

From learning how to navigate work-life balance, to having a hard time not discussing your job at every dinner, here are nine dating struggles that every bossbabe can relate to.

1. You have to push out your date nights at least a week because you’re just too busy.

So you meet an awesome guy/gal and you have your first date. Things are going great…until he/she asks when you’re free next. And you draw a total blank.

All you can think about at this moment are all the meetings, appointments, and projects you’re currently working on. “Next week?” You say, watching their face fall.

But it’s true, you probably don’t have a free minute for at least 3-5 business days.

2. You schedule your dates in your planner or calendar app.

Once you’ve committed to a date and time, you’re quick to add that to your planner or calendar app. You know if it’s not actually scheduled in there, it’s not happening.

3. You unconsciously answer your phone with your first and last name, even if it’s a personal call.

You could be seeing a person for several weeks and still unconsciously pick up your cell and answer like you would for a work call—”This is Marisa Donnelly.”

Nothing like the impersonal approach with someone you’re really trying to get to know. 🙈😅

4. You like to pretend you’re great at work-life balance, but you actually suck.

When your date asks you about how you manage your company and your social life, you smile, laugh, and toss your hair back dramatically.

“Oh, it’s easy!” You say as you nudge your cell phone (with your work email open, in mid-draft to your assistant about rescheduling that 2 PM meeting tomorrow) under the fold of your purse.

5. You like the idea of spontaneity, but it often makes you anxious.

Although the idea of getting in a car and driving to an unknown location or heading to a surprise dinner sounds heavenly, the thought of not knowing, not planning, and not being mentally prepared sort of freaks you out.

Besides, if you don’t know where you’re going, how can you know what to wear? Business casual??

6. You never know how to handle the ‘paying for food’ part of the date.

At the end of every date, you have this restless urge to reach and grab the bill before your date even has a chance to look.

You’re a hard working woman —you can get this round of drinks! To you, it’s an honor to be able to pay for things and to be seen as an equal. But you do love the idealism of chivalry, too. The ‘who’s-going-to-get-this’ is an inner (and often personal) battle you face every time.

7. You can’t shake the feeling that you have to pick between your job and relationships (even though you know that’s not true).

The biggest bossbabe dating struggle is that although you fully recognize that you don’t have to pick your career over your relationships, or vice versa, you’re still caught in that mental state.

It’s hard to let someone in because you don’t want to have to prioritize them. Yet it’s hard to walk away from them because you know you need to take healthy breaks from work sometimes.

8. You’re unapologetically passionate about what you do (even if you recognize it’s a bit annoying).

AKA you can’t stop talking about work.

While you shouldn’t ever apologize for being someone who’s passionate about her job, you have to acknowledge that this can get old after a while. When it’s dinner number four and your date stifles a yawn as you go through the process of editing your operating manager’s business proposal, it might be a sign that work has taken over your life.

Passion is good, being selfish about all your conversations is not.

9. You find yourself pushing good people away just for fear of being distracted from your job.

You love what you do.

But perhaps, underneath all the hard work, motivation, and organization apps on your phone, you love to love, too. The only way you’re going to find yourself in a relationship, though, is if you’re willing to let someone in. Fully in.

A bossbabe dating struggle is pushing the good ones away out of fear.

Just know this—the right one won’t make you compromise on what you love. The right one won’t force you to choose between your career and him/her. And the right one will appreciate the passion you have, not want you to change.

So hold out for that one.

There are plenty of ambitious, driven fish in the sea.


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