I have been apartment hunting lately, just looking to fill an empty room in someone else’s apartment rather than either rent one myself or put together a group of friends and find a place together. It has always been my experience that roommates work better when your lives are separate. In any case, Craigslist rooms are at a premium here in Manhattan, and so I quickly realized how important it is to sell yourself properly when you go to “look at the apartment.” Of course, the first thing that came to mind was pickup.

In the process of apartment hunting, I found it important to lead with my deal-breakers first, so that I don’t waste my time.  I have a few of these: I need to be able to smoke weed, at least in my room; I need to be able to cook at least a few times a week; I need to be able to bring girls back to my room without consideration of other roommates; I need to be able to fit a queen size bed in the room; I need to be in a certain location to make pulling easiest. This is an important lesson for dating too, particularly as it relates to online dating, though it’s talked about in the community pretty extensively. Don’t try to be everything to everyone, figure out what you want, and work toward designing your game to attract that type of person.

In talking with the people, since the competition is so high, you really have to sell the lifestyle that you are looking for, or at least that you think they are looking for. Job stability is an important element in this, as is savings level. Also, how will having you in their life improve their life? These are the questions you need to answer, ideally before they come up. The reason that I bring this up with regards to dating is because it occurs to me that in the past, I have not done a very good job of painting a picture of what a life with me would be like. Part of this is intentional, I generally like to choose interesting things to do on dates so that we have “fun.” Of course, any way you slice it, this is coming from the wrong place. Something that I’ve started doing lately, at least with my 2nd and 3rd dates, is trying to strike a balance between being “awesome guy” and being “chill guy.” More than that, I have been intentionally designing my dates to work with each other as a means to paint a picture of what life with me would be like. Part of that is going super meta and talking about how masculinity and femininity define each other, but part of this is also toning it way down and just strolling around the park bullshitting about nothing in particular. Maybe picking up some food along the way.

To say this another way, don’t oversell yourself. The more normal you seem, at least from a lifestyle perspective, the more she will be into it. Once you have her attracted, once you have her into you, it’s all about selling the lifestyle that you two would have together, at least if you’re looking for a girlfriend. She’s not looking for a party animal for a boyfriend. She’s not looking for a guy who can pick three awesome dates that are super fun and involved. One or two of these thrown in there occasionally are good, because women do want to have “special” nights from time to time, but in general, err on the side of being normal. Always ask yourself, “what would Don Draper do?” Yesterday I basically just walked around the park all day with a girl for a second date. It went pretty long, and ended up turning into grabbing food and watching a movie, but this is just because we were having fun. In planning the date, I had planned on doing some wine drinking with some miracle fruit, which would be fun, but is also a little ridiculous and unnecessary. Along the way, I just decided that it was unnecessary and that coming prepared with a blanket to lie on would be sufficient. Miracle fruit tastings are decidedly not what Draper would do.

Another point along the lines of not overselling yourself, at least on second and later dates, is that silence is okay. In a lot of ways, the more silence you can get away with without it getting boring, the better. If you guys are going to be dating, you will be spending a lot of time together, and she needs to feel comfortable with that silence.

Posted on Monday, July 11th, 2011 at 6:27 pm