How Should a Guy Prepare for a First Date?

You landed the first date with a lady, congratulations! Now your task is to get yourself ready for it. What should you wear? Should you get a gift? What kind of conversation topics should you bring up? Where should you go? Help! Let me tell you about my first date. I'm the type of person that can go all out when I'm able to and really want to surprise my wife. I like to think through an evening from head to toe, start to finish; I'm quite thorough when I want to be. I never like to mention too many details to her but I'll ask certain questions in case I'm not sure of something and want to be sure I get it right. I remember our first date, we were still friends. I wanted to start going out with her and I had it all planned. We were going out downtown and we made it a dress-up date. We started with dinner at this restaurant called Bandera... then we went dancing in Grant Park (I had my own makeshift stereo system which was a portable CD player and some personal speakers). After that we took a horse-and-carriage ride through downtown Chicago near the Gold Coast and finally we had dessert at a nearby Ghirardelli shop. Once that night was over we started talking about beginning a relationship.

The advantage I had, I believe, was that we had been friends for about three years prior to that date. I highly recommend that before starting any relationship that you get to know the person on a friendship level first. It'll give you a great advantage going into a dating/courting relationship.

Your first date doesn't have to be like mine, but I want to help you think through it the same way that I thought through mine. I believe that if your date sees how much thought you put into the evening you'll both enjoy it a great deal.

Transportation

I'll assume that you have a car, but if not, let's see what your options would be. You could ask her is she is willing to use her car for your date. If you do that, I would still meet her at her place but I'd get there the best way I can and get back home in the same fashion. Remember man, you're trying to impress her and be a gentleman. I'm a believer that a guy should pick up a lady and drop her off afterwords whether you're driving or walking... which brings me to my second point about transportation. Perhaps if transportation is a problem you go somewhere you can walk to. Let your date know to wear comfortable clothes since you'll be walking. Don't go anywhere three miles away, stay relatively close.

Where should I take her?

On the first date I don't recommend pulling out all the tricks up your sleeve. You want to impress but you don't want to intimidate either. Remember, this relationship is new to both of you; you need to grow into it. You also need somewhere to go from the first date. If you pull out the top hat and tails on the first date, what will you do for the encore? I'd recommend going somewhere where you can talk and enjoy each other's company. Go to a relaxed environment, perhaps a café or restaurant and maybe a movie afterwards. The goal of the first date is to learn more about the lady you're with... not necessarily her life history, but just get into the flow of the relationship.

What should I wear?

Unless the environment permits it and you both are aware of the dress code of the venue, go semi-casual. Khakis are always safe. A button-down shirt is fine as well, a v-neck sweater might add a nice touch. If you have some in-between shoes that compliment the outfit that could work.

Do you need to buy a new outfit for your first date? I don't recommend it. You probably have something in your wardrobe that will work just fine. More than likely she's seen you in certain things before so you don't have to introduce anything new. Just make sure what you have is clean, pressed, and presentable. No food stains or anything like that.

What should I get her?

No diamonds or elaborate gifts on the first date. Let's keep it simple guys. Again, don't freak her out. You have to build a relationship and build into a relationship. If she's a reader, perhaps a good book that you like. That'll give you something to talk about as well. Flowers are appropriate, as long as it's not six dozen. We're going for simplicity here.

What should we talk about?

The answer to that question is anything and everything. You'll find as the evening goes along who may be the talker of the two. For me and my wife it tends to be her. I'm good at follow-up but initiating conversation is not my strong suit unless I'm going in wanting to talk about something. Stay abreast of things going on around you or in your area. Our world is full of things to talk about. Think of things that help you learn her better as well, but don't pry anything out of her. She should feel comfortable talking to you.

Should I give her a kiss goodnight?

As much as you may want to, leave this for later. Again... grow into the relationship. Once you start introducing physical intimacy the brain does some funny things to a guy (and to the girl as well), especially if you've never been exposed to it before. If you've never had anything more than a hug then you don't want to start touching and feeling and kissing and such as it can lead to a "good morning, what do you want for breakfast" that neither of you are prepared to deal with yet. A simple ending conversation outside of her place and walk her to her door are fine and appropriate. You may find yourself in a position where you really love talking to her and that's great, but also keep in mind what time it is when you get back to her place. Perhaps save it for a phone conversation if the time gets too late.

Now that you've read these tips there's just one thing to say... have fun! Don't get so worried about the details that you don't enjoy yourself. Everything may not go according to plan, but if you can think well on your feet, improvise when needed, both you and your date should have a great time... and who knows? A second date may even occur...