Startup Studs: Here Are the 5 Keys to Dating in Tech

Startup Studs: Here Are the 5 Keys to Dating in Tech

Having spent the better part of my adult life as a philandering heartthrob, I often imagine myself as Julio Iglesias (the 30 years ago version), George Hamilton (20 years ago), and David Hasselhoff (the current version) – revered by the masses, yet also looked upon as an aging sleazebucket. For the last five years, I’ve been known by the moniker “Silicon Valley Bachelor” – or “SVB” for short – all thanks to my blog. I’ve navigated the tech scene, liberally thrown around three-letter acronyms, pinched my chin and squinted my eyes at strangers in an attempt to seem interested in their startups, and, finally, I’ve dated.

If you’re involved in the startup technology world, chances are I won’t have to break this to you, but there will be slim pickins’ when it comes to females at conferences, tech events, and startup parties. That’s why I like to make a beeline straight to the free alcohol (and free alcohol is abundant in the Valley) and drink myself into oblivion. When that happens, I like to keep the party going at home and find my soul mate on Second Life. That’s where you’ll find the hottest avatars around. They make Jessica Rabbit look like a nun.

At the risk of sounding offensive, some of the partiers I know in the tech scene, who can actually “pull” girls outside of their laptops, all routinely find the girls who go to tech events to be rather annoying. Not the girls who can actually code, or are entrepreneurs, but the ones who like to go and feel like the belle of the ball. They’re usually involved in marketing or PR, and live for the 10-to-1 ratio that has elevated them from a normal “6” on the street, to a “10” on the tech floor. They laugh and mingle; every true tech geek loves them because, for the most part, they haven’t been this close to a girl since sitting next to one in freshman year college courses.

I don’t know why you would, but if you do decide to try and date within the industry, know that there will actually be MORE competition for these girls than those outside of the tech world. The one good thing you have going for you is that you’re competing with a bunch of computer dorks. Here are some tips to remember – in a numbered list format, because people like lists (as opposed to rambling paragraphs):

1. Read the Signals
Unlike other occupations, like doctors, lawyers, or fast food employees, when tech sector employees gather they tend not to get wasted with the sole purpose of making bad decisions. It sucks. People don’t wake up with storytelling regret. They wake up with a checklist of things they didn’t accomplish the night before. Therefore, when you meet someone at a tech event, almost everyone has an ulterior motive. Networking. Business Development. Social Mobility. Girls you meet might be feigning interest so that they can gain an introduction to your investors. Or that contact you have at TechCrunch. Or, in my case, they want neither, and want me to desperately leave them alone as soon as possible.

2. The General Invite
If you’re getting mixed signals, the best way to gauge a gal’s interest – while not mortgaging the future on a potential business contact– is to ask them out to events where there will be other people. That way, it can still be a “business”-type invite. If she comes with a girlfriend, that’s a good sign. If her eyes light up and she seems receptive to a hug greeting, that’s an even better sign. If she agrees to the tequila body shot, complete with lime in mouth, you should start making wedding plans.

3. Pick and Choose
If, while talking to a girl you’re attracted to, you find out you actually would like to do business with said person, you should take a step back, focus your drunk eyes, and fold your arms so that the Drakkar Noir no longer reeks from your pits. Say some intelligent things, like: “Who are your investors?” or “What coding language is your site built on?” While you may have no intention of using the information you attain in any practical manner, it’ll make you sound professional and like you know your sh*t. My typical response to their answers goes like this, “(nodding head) Okay, okay. I like that investor/coding language. Not who/what I would’ve gone with, but they’ll help when scaling.” The word “scaling” is big time in the valley. Use it liberally.

4. Be Assertive and Confident
…Sometimes. You’ll just know. She’s laughing at everything you say, touching your arm or leg, repeatedly, throwing back her hair, blushing, and she has no intention of going anywhere. At this point, be swift. Make your move and don’t beat around the bush. Say, “Hey, you want to grab some dinner with me some time?” Or, if you’re talking about the local ball club, a theatre production, or a great restaurant (and she shows the same interest), pounce on that opportunity! “We should go catch a game of the World Series Champion Giants – best baseball team in the world.” (Because that’s how people talk and you’re only stating fact.)

5. Respect
The Valley is small, as is the Chicago tech scene and others around the country. Treat everyone with respect, even if your date turns out to be WAY better than you at Halo and World of Warcraft (that’d be a deal-breaker for me). I can literally (in my mind, anyway) connect with anyone in Silicon Valley through three degrees of separation. It’s not that I know that many people, but the Valley is really that small. In fact, I don’t even know IMPORTANT people, only like the drug dealers, strippers, bouncers, and late-night pizza employees. It’s them who can get me to that extra degree towards the Ron Conways and Mark Zuckerbergs.

So, while I highly recommend you date outside of the tech community, I do realize that sometimes an opportunity presents itself. Sometimes you’re so busy getting your startup off the ground that you don’t have any other choices. If you follow my tips closely, you may be able to seal the deal without hitting a snag… or, you may end up a pariah in technology circles. But, hey, look at me! I’m doing just fine! People leave me alone when I’m ordering double lemon drop shots for one. I can swallow sadness in peace. If you don’t mind, I must now go and fill up my flask. I bought a funnel for it. See? I scale everything.

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