In the middle of the night, I thought about the two things that keep most men and women awake at night, namely work and relationships. At this moment, I remembered how many people said that working (and especially at a startup) is like a relation, and sometimes a pretty consuming one. Then I thought of my ex-es (the startups, not the other ones ;)).

It always starts with mutual admiration. You will like her (without loss of generality, her refers to the startup). And as usual, when you get the goosebumps and butterflies, you try to impress her. Let’s assume you know a friend of her (an acquittance, an early employee, ..etc.). S/he sets a meeting for you (in the form of a casual chat with the big one there). You flirt, she accepts the flirtation. And probably if she really likes you, she will flirt back. “Oops, I did it again” said Cupid ;).

So you both like each other from the casual setup. One of you will try to setup a real date (in the form of an interview). Now the stakes are high, both of you want to impress the other. You prepare your A game, and she will too. It will start very similar to the first flirtation meeting, but this one will escalate really quickly. You will start to know her much better (if she feels comfortable around you), you also need to give her something too. Remember, you are probably starting a relation, it is a two-way road. So you start expressing yourself, in a way that impresses her (don’t worry, she’s not telling you her flaws as well). Right now, you should feel a connection, if you haven’t felt it that’s a bit of a red flag and don’t take any decision quickly.

Let’s assume you felt the connection, and she did as well. You will probably want to meet again. As of many relationships, there is someone who’s always insecure, doubtful, and needs to calculate his/her steps very carefully. Usually the startup is that one (if you are thinking of working in a startup, I really hope that you are not insecure nor doubtful). So you setup another date, some startups will prefer a hands-on (no pun intended, seriously) date, to make sure that you fit-in and can absorb her. This hands-on can be in the form of a small project to work with the team or solving a problem they are currently facing (maybe a made-up problem, but this serves the purpose). Others will continue the dating game a bit longer, they will go out once, twice, thrice and maybe more. Bear with it, you should have fun in those dates (they are dates after all, and you’re probably getting free coffee). Remember, “If she’s amazing, she won’t be easy. If she’s easy she won’t be amazing. If she’s worth it you won’t give up. If you give up, you’re not worthy” — Bob Marley.

Let’s hope everything went well. You both showed commitment and passion. You think you can pull it through. Then, and unlike any other relation, she’s the one who’s proposing!

It’s a total different level in your relation. Different dynamics, different feelings. Teen-like love is over. No more crushes. The actual story has just begun.