Bored Jewish Guy had an awesome post about a guy's thoughts leading up to and throughout a first date. He challenged girls to do it, which some have (Not Far From the Tree, (not) The Girl Next Door and Up the Beanstalk, and Bad4 has been updating the list of people who do it), but I think another guy's perspective may be necessary, so here goes.
Shaving and showering are obviously mandatory, along with teeth brushing. The only question is shaving during s'firah and the three weeks. (I'll save that for a different post). I don't spend a lot of time picking out clothes. I don't wear suits, nice pants and a button down shirt will do, and I read somewhere that girls base a lot of their judgment on the shoes, so I make sure to wear the brown shoes with the brown pants and the black shoes with the black or gray pants. Blue pants get tricky. I spend time going over directions and time. I despise relying on the GPS, so I check out google maps or hopstop (mapquest has never once steered me right) and check up directions to the house/apartment/dorm and to the destination (more on this later) from her place of residence.
The Drive to the Date
I usually listen to something mindless on the way. This could be a game or sports talk radio. I always make sure to leave it on a CD that I like so that when I start the car it gives me a chance to see if she recognizes it and it may give us something to talk about right off the bat. If I'm on a subway I'll take something with me. It could be my Zune (don't judge me), a book or even some school work which I need to finish. I always make sure to the best of my abilities to show up 5-10 minutes early and wait in the car or around the apartment building until I feel it safe to make it known that I am there. I don't want to seem too anxious or too confident.
Out of the NUMBER CENSORED girls I have gone out with, only one lived with her parents, so I have little experience in the meeting the parents department. Usually, I will call the girl and let her know that I have arrived and wait patiently for her to come down. There seems to be a problem with the Stern elevators and it always takes approximately the length of the Roosevelt administration for her to come down, but I wait it out. As is the case with most of the girls I have dated, I know what she looks like (either from a previous encounter or a picture) so I usually know what to look for. The first words will always be awkward. I will usually say something stupid (like usual) like "shall we?" and we're off.
My car is very date-unfriendly. It has no remote or keyhole on the passenger side. Opening the door is decided for me. I can't do it. It's not possible. The only option is leaving the car unlocked, but I live in New York. This is not going to happen. I unlock the door from my side and hope she doesn't hate me. I usually come prepared with two or three (sometimes four) options. The first question is always "are you hungry?" If they answer "yes, " we need to decide on milchigs or fleishigs. If they answer "no," I use my two "go to" places. I hate lounges. they are dark and weird. I usually will go to a Barnes and Noble/Starbucks in the winter. this way, if the conversation ever gets dull, you can walk around and look at the books. There will always be some topic I feel confident talking about. In the summer, I like going to the Staten Island Ferry. Girls love this place. Many have never been on it and have possibly never been on a boat at all (plus it's free). However, these two answers are never the case and we will usually discuss our hunger patterns in semi-intricate details until we decide that we're not hungry or maybe we are. Anyway, it's time to start the car. Music comes on- works like a charm. I let it play for 3-5 seconds and BOOM, instant conversation. Musical tastes dominate the rest of the ride.
I don't usually have trouble finding a topic of conversation. Both go to places have conversations built into them. Barnes and Noble has books and the ferry has the scenery. Dinner dates are easy as well. If all else fails, you can talk about the restaurant or other people there. Cafe K is a great place to play "count the dates" (record is 14). I also like to gather information that might help me come up with a second date (usually an activity). I try to see if one of the things mentioned can be turned into a date and make note of it. I don't worry about excusing myself to the bathroom or asking a waitress for some napkins or ketchup. I just do whatever comes to me.
It's always difficult talking more in the car once you spent the whole night talking, but there is always more music to talk about. Sometimes I'll let her choose a CD and we can listen to something on a really low volume while we talk. If it is a song she likes, she might interject with commentary here and there. I will always, ALWAYS get out of the car and walk her to the door. Once or twice I have been offered to come in for a drink. I will always refuse. This is classically the most awkward moment every time. I will always go back through a shadchan after a first date. Saying goodnight can sometimes take longer than it should and often end with Michael Kaye's "see ya." I turn and she closes the door. End of date.
It's usually not difficult. Did I have a good time? Were there any outstanding issues (completely different directions, looks, personality problems)? Based on these answers, I make my decision. Only twice did I not go out a second time. In other words, there needs to be a glaring reason not to go out again.