How to Date Women

There seems to be desire among the men in my peer group for more knowledge about how to date women. As a straight woman with many female friends, I believe I can shed some light on how to initiate relationships with (20-something, well-educated, high-achieving, urban, living-in-America) women*.

Where to Meet Women
I have some sympathy for men trying to meet women. As a grad student in a male-dominated field, I had a difficult time looking just for female friends.

Classes and parties are the standard recommendations: I found these to yield moderate success. I made a few (most activity-partner) friends at yoga and acrobatics. I made zero friends at dance classes because of my poor skills. Making random friends at parties requires effort: first an exchange of contact information and then subsequent attempts to meet up.

I had significantly more success meeting women through my friends, especially my female friends. There are good reasons for a single man to maintain platonic opposite-sex friendships: women tend to trust their female friends and also tend to stay away from men their friends have had relations with.

It is useful to make your intentions known. A professor once told us he found his wife by telling a few friends what he wanted and having each friend tell a few other friends. Eventually, word got back to him of a woman in Chicago he might like. He flew to meet her. They married.

Online dating is also an option. Besides the more serious sites like eHarmony and Match, more casual (and free) sites such as OKCupid and Plenty of Fish can be great ways to meet women.

You should avoid pursuing women you work with. Unless they show extreme interest, they will probably appreciate being left alone.

How to Approach Women
It is incredibly empowering to have the confidence and know-how to walk up to a woman and talk to her. (In fact, “pick-up artist” Jerry Tran has made a career out of empowering men in this way.) Think about approaching a woman like you would approach someone important at a conference: you want to make a good impression, but you do not want them to remember you as an idiot or sycophant.

Besides appearing confident and relaxed, your main goal should be to appear interesting and interested in her. An example of a good ice-breaker is a witty comment about something going on around you: for example “Seems like they stole this playlist from my middle school dance!” Another way to strike up a conversation is to identify something interesting about the woman (an accessory, something she is carrying) and ask her about it.

Here are some things that are less good to do:

• Ask if you may introduce yourself to her. Just do it.
• Comment on her beauty. Not too creative.
• Open with an offensive remark. A self-respecting woman will walk away.
• Go from woman to woman with the same lines.
• Stand around the woman for a long time without talking to her. This is just awkward.

That said, most women are polite enough to talk to people who approach them. You should not be intimidated to talk to a woman who you think is cooler, smarter, and/or better looking than yourself. You must have some redeeming qualities she could appreciate. Figure out what those are and convey them to her.

If you are nervous about meeting people, you may benefit from this advice I gave a friend for giving a talk: take deep breaths to trick your parasympathetic nervous system into relaxation mode. Remember you are awesome; visualize what you want to happen.

How to Ask Women Out
Most women like men who are not afraid to go after what they want. If you want to ask a girl out, the most important thing is to do it.

Here are some techniques for asking a woman out:

• Determine common interests and find a related activity (examples: restaurant, concert).
• Ask if you may call--you need a certain amount of (perhaps Southern) charm to pull this off.
• Get her number or add her on Facebook. Ask her out after chatting or texting.

First dates are usually weeknights: weekend evenings are valuable social real estate and weekend dates signal either a less-than-full social calendar or a high amount of interest. You should also ask for a date at least three days in advance.

Here are some acceptable dates:

• Coffee, lunch, or drinks. This could be interpreted as a date or more casually. Some women may be more comfortable with this because it allows you to explore your chemistry and compatibility without too much pressure.
• Dinner. This is usually a more serious date since it is a bigger time commitment. For a first date it is probably best not to go somewhere too formal.
• Social event. It may be good to make it clear that it is a date, perhaps through the type of event (for instance, dinner party) and/or the way you interact with her during the event.

Here are some behaviors to avoid:

• Deciding unilaterally on a time and location.
• Being obsessive about planning the date.
• Persisting when she does not show interest.
• Becoming angry when she rejects you.

How to Go on a Date
Many male friends have wondered what modern chivalry looks like--or if this is even a legitimate concept. Holding doors, helping with coats, and pulling out chairs are charming unless they feel overdone or chauvinistic. Paying is a trickier issue, especially on the first date: some women expect the man to pay, some like to split, and others like to pay. The safe route is to offer to pay. Most women will probably want to split the bill after a few dates.

On the initial dates, it is a balancing act not to scare the woman away while still revealing key aspects of your life. It is best to avoid in-depth discussion of previous relationships, family issues, and other potentially sensitive topics. Your date should not become your closest confidante after only a couple of hours of conversation.

You should take care in your appearance and dress appropriately for where you are going.

It is important to show up on time.

She’s Just Not That Into You
There are many reasons a woman may not be interested: you are not her type; she is focusing on her career; she loves another. Here are some signs:

• She does not say yes.
• She says she is busy during the proposed time and does not offer an alternate time.
• She tries to do something more casual than what you suggested.
• She invites her friends to the “date.”
• She tells you she is not interested.

If it seems like a woman is rejecting you, it may be acceptable to ask for clarification. If a woman rejects you, you should not ask her to introduce you to her friends.

Working on Yourself
If you are not meeting or dating the kinds of women you like, it may be time to work on yourself.

Small details can make a big difference. A friend’s physical therapist once told him never to skimp on haircuts and shoes. A female friend suggests that men take care in grooming (nails, facial hair, eyebrows) and personal hygiene (shower after physical activity; wear clean clothes; wear cologne on occasion).

It may be useful to have goals about an image you would like to cultivate. I have a male friend who, whenever he updates his wardrobe, carefully considers the male archetypes he aspires to be and optimizes his purchases to bring him closer to these archetypes.

That said, attractive men have a clear idea of who they are and what they like to do. You should spend time developing your hobbies, interests, and values. We may find them incompatible with ours, but we will respect you for knowing who you are.

Parting Words
It is best to start with an idea of your goals: what kind of woman you would be most compatible with and what kind of relationship you are looking for. Remember to have fun: whatever happens, your experiences can teach you a good deal and provide you with interesting stories!

* Those pursuing more casual arrangements should have a level of game outside the scope of this piece.