I moved to New York this summer and have been meeting women online and dating ever since but I feel like I’m terrible at it. I never know what to say on a date, I feel tons of pressure to make clever/witty remarks, I hate the awkward silences and I basically feel like it’s an ‘interview’ over and over again. What’s worse is that after a date, I usually can’t tell if they are into me or what the next step is. As someone who specializes in lesbians, can you please shed some light on what women want?


‘Specializes in lesbians…’ Now there’s some pressure. Ironically, your innocent statement probably had the same effect on me as dating has on you, which is to say that the expectations are a little overwhelming. Good for you for choosing a term that resonated as it did with me. This is a loaded topic, but I’m just going to graze the surface.

I find that most people like to talk about themselves, which is good news for people who find themselves at a loss for words. Instead of assuming all the pressure to be entertaining, try asking your dates thought-provoking questions about themselves. If you’re meeting women online, you have the added advantage of knowing a little about them before you meet. Do a little homework and even the most general information can become the main ingredients for an amazing date. If one of her hobbies is art, ask her what type of art she enjoys. Find out places in NYC that offer classes or workshops in that type of art. Find out who the top artists were/are and form some questions to ask. Each of her answers then becomes a springboard for more questions you can ask.

If you find yourself cringing over the amount of effort I’m suggesting you invest, ask yourself how much energy you’d expend prepping for a job interview. My point is that we need to expend a reasonable amount of energy in our personal lives and not expect things to unfold effortlessly the way they do in movies.

Women are complicated. There are no shortcuts or generalizations that can replace or compete with having a partner who is genuinely interested in your thoughts, opinions and feelings. And fortunately, you do not have to figure out what women want – just what the woman in front of you wants. And unlike Freud, I’m a big fan of asking rather than pondering.