Inspired by a very thought provoking and insightful article on how to date a “Wall Street man”*, I thought I would perform my civic duty by providing some timely advice on this Valentine’s Day for the tech community. As a professional tech startup investor with an office in New York City, many of my entrepreneurs are very successful, high profile, yet lonely and hopelessly single Silicon Alley guys.
I have spent the better part of 12 years learning all of their habits, their likes and dislikes when it comes to dating, women and relationships and what they want specifically from women when they pause their epic Starcraft battles and take time to look up from their monitors.
Hence, I know, better than anyone, what makes Silicon Alley guys tick.
Here are a few tips for the women out there who are dating or would like to be dating a man on Silicon Alley:
- Be prepared to charm him out of talking about programming when he first arrives to the date. Unfortunately, a lot of guys on Silicon Alley have a hard time leaving their code sitting alone in Github when it could be refactored; it’s your job to get his mind on you and off Amazon S3 outages, SecondMarket valuations, and TechCrunch funding announcements.
- Learn a little something about tech markets and notice if something huge happens on a given day, negative or positive. Things like the fact that Facebook is going public is not just tech news, it’s world news and you don’t want to seem clueless if you completely missed something like that. You don’t have to become an expert but at least if you know something you can parse out the cap table with your guy. Additionally, you need to be prepared that the volatility of tech valuations might make your guy’s mood unpredictable, especially on a day that his personal equity stake went down dramatically.
- While a Silicon Alley guy tends to like a little bit of a challenge when it comes to dating, he still likes things to be convenient and easy for him. A lot of women think that if they play a mean game of Skyrim or know a Tardis like the back of their hand, they will land a Silicon Alley guy. This is NOT the case. Yes, you should be confident and avoid being a pushover but, at the same time, you shouldn’t be difficult. You need to be accommodating of his limited social skills and time constraints or he will get frustrated and play more videogames.
- Tell stories that are as short as a Tweet because the mind of a Silicon Alley guy is always moving so rapidly and focusing on so many different things that his attention span for Longreads is very short; don’t be insulted by this, just tell your stories in a way that he can listen. Save your long, draw-out Pinterest pinboards or Tumblr reblogs with your girlfriends.
- Be geeky. Silicon Alley guys tend to like women who are attractive and wear a smoking hot pair of Warby Parker’s. This does not mean that you should look sexy or hipster forward, this just means that you should bring your “Tech game” when you go out with him and know all about Fashism and Rent the Runway. Every man is attracted to a different look and a different type of woman so if he’s interested in you, he’s attracted to you but you need to maintain his interest by continuing to be your geekiest.
- Don’t get upset if he checks his iPhone or updates his status during a date; this is very common of a Silicon Alley guy and has nothing to do with whether or not he likes you. The advice that I give Silicon Alley guys about their need to bring the Internet onto the date is that they should forewarn you when they first sit down that a call or a message is coming and apologize in advance. Albeit the fact that this would be an easy thing to do, they won’t always remember to do it, so don’t get offended and Tweet bomb him or downvote his Reddits.
- Don’t get upset if your Silicon Alley guy isn’t as romantic as you would like him to be. Men, by nature are never as romantic as women want them to be, but Silicon Alley guys especially are very tech-like and think practically not romantically. If you want him to be more romantic, you are probably going to have to lead the way through location-based apps like Foursquare, and teach him what you want through a Skillshare class.
- Silicon Alley guys tend to be attracted to women who are in industries other than Silicon Alley. This does not mean that if you work on Silicon Alley, you won’t end up with a Silicon Alley man, however his eye tends to be looking towards non-Silicon Alley women. Hence, if you are a Silicon Alley woman and you are interested in dating a Silicon Alley man, you need to make sure that you let him and others see that you are not all hacker all the time, that you have a soft, geeky, tech-oriented and fun side when you are not in the office.
- When it comes to getting you a gift, a lot of Silicon Alley guys are all about the hottest gadgets over thoughtfulness. If you are a techie woman, this will work well for you, but if you are a woman who prefers a man to be thoughtful over spending lavishly on the latest gaming console, you might be disappointed. This does not mean that a Silicon Alley guy can’t be thoughtful, many are. However, a lot of Silicon Alley guys are so busy shipping product, that when they think to buy you something, they don’t care about the cost as long as it can be shipped via Amazon Prime.
- Don’t get upset if your plans get scheduled by his latest automated scheduling algorithm. Even though it is dating 101 for a man to pick up his iPhone and iMessage you for a date, many Silicon Alley guys are so reliant on their latest recommendation engine slash task management web app that they prefer to have you on their schedule just like any other VC or product meeting. Do not take offense to this; this does not mean that he likes you all the less, it just means that he likes to be organized and efficient and his algorithms helps him accomplish this.
* Just in case your sarcasm chip is not installed, I say this in jest.