[tptacek]

Correct: if your interactions with a founder are cabined by professional settings --- demo days, funding pitches, going for coffee to talk about their company --- romantic overtures are inappropriate. Similarly: if you're in process, at any stage, with a company, overtures to their founders are inappropriate.

[lisper]

It's important to understand WHY this is so: if you're an investor you are in a position of power over a founder. It is not possible in such a situation to make a romantic overture that is not tainted by the possibility that you are looking for a quid-pro-quo even if in fact you are not.

[tptacek]

In addition to quid pro quo, making romantic overtures in professional settings sets up a barrier for women that doesn't exist for men. Men can go to coffee with a potential investor and know walking in the door that they're there to get a hearing about their business. But every woman that walks through that door has to fight off the concern that the meeting isn't about their company, but instead about their own personal availability.

Even if 90% of the time that concern is unfounded, the mental effort you spend dealing with that exerts drag and hurts your performance. One of the things investors are grading you on is confidence!

[brador]

What about simply asking for his number?

[untog]

Phone number for a business conversation? Of course.

This isn't difficult. I know techies have a reputation for being socially awkward but if you're suggesting that asking for someone's phone number in a business context could be mistaken for asking in a romantic context then you're wrong. It's very, very easy to define intention.

[jtbigwoo]

Nope. The implication of quid-pro-quo would make any potential date/relationship/other an ethical mess.