So you have the conversation started, reached the two minute point, and she hasn’t maced you yet. Kudos. Now what are you going to talk about?
Again, the main thing should be her. You need to seem honestly interested in her (and, to be honest, actually be interested in her). However, if she is somewhat reserved you will have to find some things to talk to her about.
One of the best things you can do to keep a conversation moving is give her a compliment of some kind. However, be aware there are good compliments and bad compliments. Most women are more or less looking for a reason to get rid of guys bugging them and the first thing you say that they can choose to interpret negatively is their rip cord and for the most part they will pull it.
So, as always, I will start with what NOT to compliment her on.
1. Any part of her body, especially breasts, legs, or more or less any part thereof. Even something as innocuous seeming as her hands is a huge land mine. Women are for the most part massively insecure about a lot of stuff you wouldn’t believe, and something as innocent as “Your hands are very slender and clever looking” can easily trigger her pathetic self contempt for her skinny fingers. Also, mentioning any part of her body that can be interpreted as a sexual turn on (and for most guys, that can be any part of her body) will put you permanently into the creep category. Stay away.
2. Most of her clothing. There are a few exceptions to this, but most women use clothing to hide the things they feel insecure about and mentioning it will only reminding them about it. Also, complimenting a woman on her dress is an open invitation to throw out a “Does this dress make me look fat” trap for which there is no good answer.
3. Any observed perception of what you think her religion, politics, or other agenda may be. This is all fodder for the first and second date. Don’t mess around with it.
Ok, so what can you safety compliment her on? Here are a few items.
1. A very general appreciation about her looks if she looks dressed up. “You look fabulous.” Don’t get into specific items.
2. Shoes. Women love shoes (I have a theory on this, but won’t get into it today). They seem to love compliments about their shoes, especially if it looks a little different from what every else is wearing. In my experience, if a woman is wearing boots of some kind (especially if they are unusual color boots or have tassels or something hanging off them) she is fishing for compliments on her footwear. Don’t disappoint her.
3. Jewelry. This is another category of things women wear to get compliments. Necklaces, bracelets, earrings, and rings are all open to comment. HOWEVER, if she is wearing a pendant that is combined with a really plunging neckline and some good cleavage comment on her earrings.
Hey, Diana. Nice bracelets!
(image courtesy of the comic book t shirts)
4. Handbag. This is a weird one, in that some women love handbags and will literally spend thousands of dollars on a single bag whereas others don’t really care much at all and throw their stuff into whatever sack they have lying around. However, in general the smaller the bag, the more worth of a compliment. Also, it is worth your time to go to a high end department store and learn what the logo’s of the higher end bags looks likes and compliment her on her bag by name (“Is that a Prada bag?”). If a woman is carrying around a $3500 handbag she is most likely so desperate for a compliment on it your comment will feel like the first breath of air after being trapped under the ice, if you know what I mean.
5. Hair. Women spend a lot of time on their hair, and for the most part appreciate a good compliment on it. Color (as long as it’s not gray) comments are generally well received if it is obviously an artificial color (“Your hair has the coolest green highlights”) but stay away if it looks like she is attempting to look natural, even if it is painfully obviously not her natural color.
6. Any apparent ability she has, especially if it something “fun”. Tell her she is a great dancer, runner, drinker, or whatever (“Wow, you can really hold your own on these Jager shots”). Everyone loves being noticed for some kind of ability.
That’s some good guidelines. As always, remember that things are all situational, and keep in mind that two minute rule.