I think that the place someone picks or suggests for a first date can, in some cases, tell something about them. Perhaps a female would have better perspective than Isince, as the asker-outer, I am normally the one who ends up suggesting the activity or meeting spot; I would still like to offer up my two-cents on the topic, anyway.

As someone who puts a great deal of consideration into where to take a woman on a date, I am always trying to suggest places that will we be different or off the beaten path. Therefore, if a woman was to suggest to me that we go to a generic place where everyone and their brother knows about, I might be slightly put off by the lack of imagination in their suggestion.

You see, for me, a first date is a time to test people a little bit – see if they are really willing to try new places and venture away from their neighborhoods to explore all that the city (of Chicago) has to offer. I honestly think that it’s fun to take people out of their comfort zones a little bit by taking someone to place that they admittedly haven’t been or to an area they don’t frequent very often.

Tonight I am going out on a date with a woman, at her suggestion, to a restaurant whose cuisine I haven’t ever tried, in an area that I’m not very familiar with, and to be quite honest am very excited about our impending adventure. This isn’t to say that if a woman suggested a generic place for a first date that I would write her off, because there is something to be said for that approach. HOwever, the fact that this woman would suggest this particular restaurant for our first date indicates something cool about her to me that I am looking for a in a woman.