[acabrahams]

Yes. You are generalizing. Massively. There is no possible situation in which a VC I had met could ask me out without making me feel extremely uncomfortable, to put it lightly.

There are lots of logical reasons for this reaction, and I will list some of them briefly. 1) Power of VC network is implicit threat to 'play nice' and go along with it, even if VC in question has no intention of being nasty in any way. 2) The power imbalance already implicit in VC/founder relations makes 'asking me out' incredibly tense. 3) It would make me doubt myself- "Is every other VC I am talking to (since they are 90% men) just interested in me for that reason?".

So follow the OP's advice. And just don't do it.

[balls187]

The reasons you list are often cited reasons why managers or people in authority should not "fraternize" with subordinates. You're right, very logical reasons, and why most companies frown on that behavior.

I understand that founders want to be taken seriously, and and investor blurring the lines between professional and personal relationships can jeopardize that, but not all relationships with investors are like that, and I'd imagine not all founders would doubt themselves if approached after the fact.

I am biased, because in Seattle, the VC community isn't as threatening from a "play nice or else" perspective.

Also, I'm a sucker for romance and the boy meets girl, and live happily ever after story.

[afro88]

I think balls187 left off one important point as a VC: make it clear that you aren't interested in investing in their company, but want to go for coffee/lunch/whatever on a purely personal basis.

As a founder, the discomfort comes from not knowing the VC's intentions and how you are supposed to act with regards to your company. The VC needs to draw a clear line (ruling out investment and all other professional involvement) that takes a lot of that discomfort out of the situation, and removes the mixing of business and pleasure.

[balls187]

> make it clear that you aren't interested in investing in their company, but want to go for coffee/lunch/whatever on a purely personal basis.

You're 100% right (which is why I said don't mislead).

However, this is far more nuanced, than I first imagined. From purely a dating perspective, I'm not sure how a guy could recover from rejecting a women professionally, to getting her to accepting a date.

I guess the circumstances would have to be something like investment thesis don't align "we do biotech, your company is education."

In startups, I'd argue that founders personal lives and their businesses are inextricably linked, and rejecting one, is tantamount to rejecting the other.

Which makes for an inbalanced dynamic as acabrahams mentioned, which could be troublesome.