You know that age-old adage about not dipping your pen in the company ink? Let’s forget about the crude imagery that saying implies and focus on the real question: are office romances always off limits? Specifically, is your cofounder’s love worth risking your company’s future?

Pros and Cons of Dating Your Cofounder

Cofounders flirting on date in a restaurant
Cofounders flirting on date in a restaurant

The pros of dating your cofounder seem pretty straight forward when you consider all the time you spend with this person. After working long nights and countless hours hashing over investment deals, it’s likely you’ve developed a deep bond. You’ve come to depend on this person for emotional support. You admire how they handle themself in difficult situations. When you’re running your own company, it’s likely you don’t have time to see other people and your cofounder can fill what’s missing in your life. This bond you have created can turn into something romantic and special.

The downside of dating your cofounder is you spend all of your time together. There’s a difference between going home to the person you love and letting off some steam versus going home with the same person you probably want to vent most about, but can’t. Because you never get a break from your cofounder, this can lead to animosity in the workplace. Suddenly, that annoying thing they did at home finds its way into the office and vice versa.


You obviously place a lot of trust in this person to start a business partnership with him or her. If you start dating, that trust will carry over into the personal side. You may feel you can trust them with your sensitive issues and past secrets. There’s no denying it’s hard to find someone you can trust with all your heart and reveal your vulnerabilities to.

However, when you’re “looking through love goggles”, you may fall victim to blind trust. Because you believe everything your partner says and does is right, you won’t want to interfere in their business affairs. This can cloud your judgement when it’s time to close a business deal or handle finances. When we’re in love, we tend to forget that our partners are human and, therefore, flawed. Everyone is capable of making mistakes and needs to be steered in the right direction once in a while.


Most couples will tell you communication is the most important part of a relationship. With your cofounder, you also have to be in constant talks in order to make things work. The benefit of a business relationship is that sometimes you have to be blunt for the good of the company. Telling someone you believe their idea isn’t great, even though it may hurt their feelings, at least creates an honest working relationship.

When you’re in a romantic relationship, telling your partner you disagree with them likely leads to some kind of argument. If this argument happens within a business environment, it will seem very unprofessional to those around you. Being blunt in a romantic relationship isn’t always a good idea, but not speaking up at work to spare their feelings when you don’t believe in their idea is equally damaging to your company.


One benefit of dating your cofounder is you’ve already committed to a long-term relationship by signing a business contract with them. At the very least, you know they are capable of commitment. That kind of loyalty isn’t easy to come across in the business or dating world.

The problem with dating your cofounder is also a lack of commitment. Obviously, if you are just considering the idea of dating your cofounder, then you are not married. Being a business power couple works for certain people because marriage demonstrates commitment. Married couples have already experienced ups and downs prior to starting a business, so they are aware of what their relationship can handle. Married couples are also more likely to work through an argument. When you’ve just started dating and things get rough, you might feel it’s best to throw in the towel. Where will your company be then?


Lastly, don’t forget reciprocation. Let’s say you think about your cofounder day and night. You may believe in your heart this is the right person for you. If they feel the same way, great! But if they don’t and you ask them out on a date, best case scenario, they let you down easy. Worst case, one of you feels uncomfortable now that your feelings are out in the open. Suddenly, you may not want to work in the same environment anymore and the company suffers.

Outside Factors to Take into Consideration

Employees working with dating cofounders
Employees working with dating cofounders
How your employees feel

Your employees may worry that bringing up any type of disagreement with your cofounder means they risk having you turn on them as well. This can make your employee feel they have nowhere to turn when things get rough. Also, let’s say you take a certain criticism nicely, but your partner does not. Are you forced to take your cofounder’s side? This type of hostility can bleed into your romantic relationship, causing more turmoil at work.

What do investors think?

Many investors are hesitant to place money into a venture with romantically linked partners simply because of the complications that can arise. If they worry your business can collapse at any moment due to a personal dispute, why would they invest in your company? However, when a couple is married, investors are less hesitant to get involved because they know the bond between marriage is stronger than dating. Marriage is a legally binding contract, after all.

Successful Business Couples

Robert L. Johnson and Sheila Johnson cofounders of BET
Robert L. Johnson and Sheila Johnson cofounders of BET

Of course, there have been many successful business couples throughout the years. Silicon Valley entrepreneur Sramana Mitra writes about a few of these in her blog for One Million by One Million. Robert L. Johnson and Sheila Johnson, for example, cofounded Black Entertainment Television in 1980. They earned the title of America’s first black billionaires when they sold the network to Viacom in 2001. Though their marriage didn’t last, their working relationship gave birth to one of the most influential television networks for African American representation today.

Dating your cofounder and having a successful business isn’t impossible as long as you take into consideration all that is at stake. Not just your romantic feelings, but the future of your company and everyone it affects. Remember, there is a distinction between love and lust. If you can’t imagine your life without your cofounder, then go for it. Otherwise, put your company first and leave your pen in the drawer.

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This article originally published on GREY Journal.

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