We walked out onto the sidewalk, laughing and sharing the inside jokes that had been formed over the last 90 minutes. We exchanged a long hug and phone numbers. He gave me another quick hug and disappeared into the Uber that was waiting for him.
I stood there for another few minutes unpacking and analyzing the intentions, events and emotions of the evening.
We had set this meeting to discuss an upcoming event he was helping me organize. I knew nothing about him except he was good at his job and had helped my friend set up a blowout fundraising event. That’s all I cared about. My friend had failed to mention he was tall, handsome and maybe-single.
I didn’t know whether he was actually single, that would be a strange thing to ask during a business meeting. But was it a business meeting?
As an entrepreneur, there is so much ambiguity. I never really stop working and rarely have meetings in a conference room. I also have an active social life that weaves between my business life. To say my worlds of business and pleasure are blurred would be a massive understatement. Pleasure is my business. It’s common for me to have a meeting after 7pm over beers, wearing bright lipstick and an outfit that makes me feel super sexy. As a sex writer – it’s good branding. And more importantly, it’s me being me.
When your life and business and sexuality blend, you have to face this question: Was that a business meeting or a date?
It matters because you don’t want to compromise valuable business relationships by accidentally coming on to someone who isn’t expecting it. (done that) But you also don’t want to pass up on a potentially amazing relationship just because you first met under the guise of a joint business venture. (that happened)
While connecting with someone on a romantic or sexual level during a business meeting is a perk of my job, the opposite is also true.
I’ve had more than a few dozen meetings with potential investors and collaborators have ended up being sneak attacks for men who didn’t have the courage to ask me on a date. They knew that by showing interest in my business they could get my undivided attention for an evening. Pulling this move guarantees that I will never ever date you.
I’ve learned that if a business opportunity sounds too good to be true, it’s probably a wannabe date.
Not only is it massively cowardly, it shows how little you respect women entrepreneurs.
As a woman, there are so many stereotypes and assumptions we are constantly fighting against, it can be hard to let down our guards to make room for romance. We are constantly fighting to be respected and non-sexualized in a man’s world.
So you can see why it feels risky to compromise that respect for a potential relationship or a night in the sack. And it is infuriating to have that respect squashed by a manipulative pussy.
So how do you set boundaries for business meetings? And how do you learn to cross that line for romance when it’s worth it?
It’s a strange feeling walking away from a business meeting with butterflies. It’s easy to spin a story and explanation of the situation in your own mind. Unless you understand the other person’s perspective, you could be setting yourself up for unnecessary rejection. You have to ask them what they want.
More importantly, you have to decide what YOU really want. Do you want to get involved with someone you work with? Is it worth abandoning your project for the potential of love? Get clear on what you want. And let that clarity sit for a few days. The excitement of new love interests can sometimes distract us from reality.
If you’re still interested when you reconnect to reality – then give them a chance to provide clarity.
No need to ask outright whether they want to have your babies, just give them a chance to clarify their intentions.
Say something like “Let’s meet next week to talk about the project at my office. If you want to do something this weekend just for fun, I’d love to get to know you more outside of business. Want to go for a drink this weekend?”
Separating the two let’s them say yes to one or the other or both.
Never fucking text message
Text messaging is a terrible way to communicate with someone new. Especially when the relationship has unclear motivations, texting will only muddy the water.
The rules are simple:
If you want a business relationship and they want something romantic, only email them. Do not text. If they text you, wait an hour and write them a polite email answering their question. Do this as many times as they need to get the message.
If you want romance or sexy-time, only call them. This is my rule for all romantic relationships regardless of where I meet them. If you’re really interested in a person, pick up the goddamn phone and talk to them. It creates intimacy and clarity. There is no room for the miscommunication that is inevitable with texting.
Do not text message. Unless it’s logistical or necessary. You’ll avoid so much self-manufactured heartache.
Sometimes you just have to go for it. Maybe you’ve met a few more times and the relationship never seems to fall on one side or the other of the love/business fence.
You’ll know when it’s time to just lay it out there. Tell them you think they’re amazing and working with them would be great, but making out with their face would be awesome too. You won’t be hurt if that’s not their intention, but you have to say it.
So many people I talk to keep their feelings bottled up and never pursue the potential for love, when they fear their business might be negatively impacted.
Frankly, that’s fear talking. And love is more important than business. period.
In the long run, finding a new CFO will be much easier than working with someone you secretly have a lady-boner (or regular boner) for.
Let romance develop naturally
Love doesn’t always happen overnight. If you honestly don’t know if you want romance or business, don’t worry. There’s no need to rush either relationship.
Let things grow naturally and let your mind wander and fantasize without having to immediately act on it. Working with someone of the opposite sex that you get along with, you find interesting and attractive, doesn’t mean you HAVE to date or sleep with them.
Let love develop naturally.