How to win a first date without really trying

How to win a first date without really trying

First dates can be can be a challenging and stressful adventure but they are also a necessary evil to overcome. Nobody likes them. Everyone feels a bit of uneasiness and awkwardness during a first date. There are the rare exceptions to the rule when two people that have been friends for years decide that they want to try something more romantic. However, most of the time a first date is a terrifying prospect.

Even with all that can go wrong with a first date there are some easy steps you can take to make your first dates more comfortable and smooth. As an expert in the field (I’m not) I’m here to help you develop a first date strategy that is guaranteed to make you succeed in your dating life. Having successfully landed a mate that is, without question, far out of my league I can state that by following these simple steps you too can land the woman of your dreams. (Note: As I am a heterosexual male these steps will be written in a manner that will allow a man to have a successful first date with a woman. However, these steps can altered by simply changing the pronouns for a woman to successfully plan a first date with a man, a man to have a successful first date with a man, or a woman to have a successful first date with a woman.)

Step 1: Laying the Groundwork

A successful first date best begins before the first date is even scheduled or planned. It has to be because the laws of physics require that one person at least know of the existence of the other person before a date can be planned. If you want to be successful like I was you first must meet someone that you find interesting and then you must make yourself appear interesting to the other person.

The first time I remember meeting Rizzo was on September 19, 2009 (HA HA, take that Rizzo I do know the exact date) (Please don’t yell at me if I get these dates wrong). I say the first time because we were at a wedding of our mutual friend, Andrea, many years before but I don’t remember meeting Rizzo at that time. The same mutual friend was not in Kansas anymore and was visiting our Northern Virginia area. Since she was in town she decided to have a get together hosted at her parents lovely home to which both Rizzo and I were invited.

I had just moved to lovely Stafford, Virginia at the time and was happy to make my way up to Virginia to see my friends. The party also gave me an excuse to hop on my motorcycle for a nice long ride. Gentlemen, keep this in mind when laying the ground work; ride a motorcycle. Rizzo claims to this day that the fact that I rode a motorcycle was not an enticing detail of my personality but I think she is lying. I know that when I walked around the house to the back porch where everyone was socializing wearing my black boots, blue jeans, black t-shirt, leather jacket, and carrying my helmet she was in awe of the manliness that stood before her. I mean, if I could, I probably would have dated myself (those with a dirty mind insert your own joke here).

My old hog

My old hog

When you are laying the groundwork for this first date it is important to make sure you are in a place you feel comfortable. I am a disaster in most social situations. I hate meeting new people and feel completely uncomfortable and overwhelmed whenever I have to go places where there will be lots of people I don’t know but I will have to interact with. Luckily for me this gathering was a small, low key event chocked full of my closest friends. What that means is that I could completely open up and be myself, which always includes making in appropriate jokes, self-deprecating humor, and lots of bad language. If I would have met Rizzo at a bar, or a coffee shop, or some other bad sit-com location there is no way I would have ever been able to entice her or even talk to her for that matter. I would later come to learn that Rizzo is always comfortable meeting new people and has an endless supply of talking so she is good in any social situation. Creating a combination for the first meeting where both parties feel comfortable is vital in making the first date work.

After several hours of making crude jokes, drinking a few beers (this was before the craft beer boom really hit me so I’m sure they were less than quality), and playing several games of ladder golf (of which I am an amazing player) with Rizzo as my partner I decided I had to hit the road in order to get my motorcycle home safely. Our friend Andrea was kind enough to walk me out and during our few moments alone I inquired as to Rizzo’s dating status. I honestly don’t know who was more excited; Andrea to be able to tell me that Rizzo was single or me for learning that Rizzo was single. After leaving the party and making it safely back to my apartment I was able to acquire Rizzo’s digits (yes, I called them digits. Shut up.) from Andrea. A few phone calls and a date was set for the following Saturday. Now I had to plan.

Step 2: Selecting the Location

When most people think of a traditional first date inevitably a meal is involved. I’m sure everyone that has ever date anyone ever (at least in the United States within the last 60-70 years) has been a part of or known someone that has been a part of the dinner and a movie first date. I’m here to tell you that this is the absolute worst idea for a first date. The best idea for a first date is to go bowling.

Classy.

Classy.

You may think this is a joke but there is nothing funny about going bowling over going to dinner. When you go out to dinner (or any kind of meal or coffee or drinks) you are instantly forcing the awkwardness of two people that don’t know each other to come to the surface. Dinner forces you into the trap of asking the stereotypical questions you do on a first date because you have to fill the deafening with some sort of noise. “What do you do for a living?” “Where are you from?” “What do you like to do in your free time?” Questions that are necessary to be asked during the getting to know you phase of a first date but create a sense of being “forced” when you are sitting in a restaurant staring at each other.

Bowling, on the other hand, is a fun activity (not just sitting in chairs looking at each other) that allows you to ask all the getting to know you questions but also has a built in getaway if things start to get weird. It also has the added bonus of allowing you to impress your date without being to overbearing (did I mention you should be fairly decent at bowling for this process to work?)

After picking up Rizzo at her townhouse I took her out to the local Bowl America in Falls Church, Virginia. I feel very comfortable in a bowling alley thanks to the years spent on a youth bowling league, an adult bowling league in high school, and a year on the JMU bowling team. I had never been to the Falls Church Bowl America but that wasn’t a big deal because it was just like every other bowling alley in America; sort of dingy, sort of grimy, and somehow still having a slight smell of smoke even though the alley had been a no smoking establishment for years.

I don’t remember the scores of the games. I don’t even remember how many games we finished. What I do remember is that I had a thing that I could hang on to whenever I felt uncomfortable; and that thing was walking away from the conversation, even if just for a few moments, to throw a ball at some pins. I was lucky because I never felt like walking away from the conversation but that is the beauty of going on a first date to a bowling alley; if you feel comfortable talking and getting to know the person then keeping talking and getting to know the person and ignore the bowling, if you don’t feel comfortable talking and it starts to get awkward you always have to get up to take your turn and no one has hurt feelings. It’s a win-win situation.

You say you don’t like to go bowling (what kind of person are you?) and you want to do something else? Great! The point is to pick an activity that is more than just drinks and dinner. Go to the driving range and hit some golf balls. Go out and play a round of miniature golf. Take a cooking class. Go to one of those “we are going to paint but really we are going to just drink wine” classes that hear exist. Just do something that has a built in release valve for both parties involved to step away, figuratively speaking, to catch their breath to they aren’t constantly under the gun.

Step 3: Dress the Part

On your first date you will, of course, want to impress the other person with your appearance. This is of utmost importance. Make sure you take a shower and shave (yes, the shaving applies to both men and women). You may need a haircut, you may not, so don’t get too stressed out about this unless you are getting really close to the time you would need a haircut anyway. Get yourself as presentable as possible and then pick out your clothes.

Some self-help gurus such as me will tell you that you should find your very best clothes you have make them work for the date. This should be suited for the situation (you don’t want to be wearing a tuxedo to a bar. Or do you?) but I don’t agree with this one bit. Dress as if you are going to participate in whatever activity you determine in step 2 with a big group of your closest friends.

Knowing that I would be taking Rizzo to the bowling alley I decided to wear my favorite bowling shirt. It may seem a little to “on the nose” but I didn’t pick the shirt just because I think it I would look awesome going out bowling in my awesome bowling shirt. This bowling shirt was one of my favorite shirts at the time and continues to be in my standard shirt rotation. I bought this shirt when I was 16 years old working at Ross: Dress for Less in Sterling, Virginia. It still fit me fairly well, it was comfortable, and it fit with the bowling theme.

I complimented my dark blue bowling shirt with brown trim by wearing my favorite pair of green cargo shorts. Yes, I understood that cargo shorts are not the most fashionable attire in the world but I didn’t care because I was the kind of guy that wears cargo shorts. I’m still the kind of guy that wears cargo shorts. I’m sure when I’m 100 years old (I’m being optimist. Probably more like 75) I’ll be the kind of guy that wears cargo shorts. That is who I am and that is how I feel comfortable. If you don’t feel comfortable on your first date the person you are dating is going to sense this immediately and no one will have a good time. So dress like you would normally dress for wherever you are going or whatever you are doing.

Rizzo must have travelled about 6 years into the future to read this blog because she did the exact same thing. Rizzo was wearing a shirt that thereafter became known as “first date shirt” and a nice pair of jeans. She was stunning. I loved that she didn’t get all gussied up to go on a date with me to bowl. I don’t want her or anyone else to misinterpret that statement. She looked amazing and put together but she also looked like a woman that was dressing to make herself feel comfortable in her own skin. There is nothing sexier to the person you are going on a date with than being comfortable with yourself and dressing for looks and for comfort are important parts of that which is why I found her so attractive that night and every night since.

Believe me when I tell you that it doesn’t matter what your first date if you hit it off then it will become an important part of your relationship. When Rizzo and I got married Rizzo used that bowling shirt I wore on our first date as her something blue. She needed something comfortable with buttons to wear while she was having her hair and makeup done before the ceremony. I loved that she chose to wear my bowling shirt. It had a lot of meaning for me to wear the shirt on our first date and for her to wear the shirt on our wedding day.

Rizzo getting ready for the wedding with my bowling shirt prominently displayed

Rizzo getting ready for the wedding with my bowling shirt prominently displayed

Step 4: Gifts

Not everything on a first date is about being comfortable and with yourself and your surroundings. Sometimes it is about straight out flattery. That is why it is important to arrive to your first date bearing gifts.

It is the responsibility of the person who has organized the date, the “askor” if you will, to bring said gift. We are not talking about something extravagant. You don’t need to arrive at the doorstep of your companion for the evening (that sounds sort of dirty in a 17th century way) with jewelry. In fact, that is a bit creepy. Bring along something small and then turn it into a game.

You may consider bringing flowers to your date. There is nothing inherently wrong with that and is often considered a sweet gesture but I would advice against it. Here is why (1) The flowers are going to die. That is not questioning your ability to pick flowers it is just a fact of life. Once the flowers are gone so is the gift and the potential memory. (2) Flowers are uninspired. Unless the person you are dating happens to have a fascination with a specific flower like a daisy or a chrysanthemum your date, or the “askee” won’t be impressed. (3) Flowers will get in the way. What is the askee supposed to do with these flowers the rest of the night? It is really weird to have to carry around flowers the whole time and it can create an awkward moment if the askee has to take the flowers inside to put them in water while you wait outside on the front porch because you are some creep that is taking the askee out for the first time and the askee doesn’t want you in their house yet.

The key to a good gift for the first date is listening. Before the first date you will have had one, if not more, conversations to know you would like to go on a date. This doesn’t matter if you are “listening” over an internet conversation through a dating site or listening while you chat at your friend’s party. By listening you will pick up on at least one little thing that will give you an idea for a gift.

We still have the book.

We still have the book.

In the conversations I had with Rizzo before our first date, both at Andrea’s party and over the phone, I learned that Rizzo was a huge fan of the Washington Redskins Football Club. I couldn’t care less about the Redskins but I made a mental note that she mentioned the Redskins on more than one occasion. With this little nugget of information I picked up a book about the history of the Reskins while I was out getting something for myself. It wasn’t an expenses book, maybe $10. I don’t remember the name of the book (there is a picture just to the right of this paragraph so you can see the title of the book in that). I’m sure I’ll never read the book and , to be perfectly honest, I don’t know if Rizzo has ever read the book in its entirety. It doesn’t matter. What matters was the listening and the paying attention to what she was saying and using it to make an impression.

I wrapped the book up in some wrapping paper and brought it on the date to the bowling alley but Rizzo had to earn her gift. The deal was that if she beat me in any game we bowled she would get the wrapped present. If she didn’t then I would have a wonderful new book. Of course I intended to give her the gift no matter what but having a game to play outside of just bowling created some conversation and gave us both something to strive for other than just throwing a ball for the fun of it.

A small gift can play an important role in making your first date successful. It shows that you are paying attention to the person even before your first date. The saying goes that “it’s the thought that counts” and that sentiment is true. This little gift isn’t showing how awesome you are or how much money you make because it isn’t about the price. The little gift shows that you care about another person and you really want to learn who they are and what they are all about, even if it isn’t something you like. The gift makes the date feel like it is all about them and, in fact, it is.

Step 5: Seal the Deal

At this point of the date you have laid the groundwork for a successful event, selected the appropriate location, dressed the part, and given the gift. There is nothing left but to seal the deal. Get your minds out of the gutters, you pigs (yes, I clearly know my audience). All sealing the deal means is being yourself. Don’t try to be someone you are not. You aren’t a millionaire so don’t try to spend like a millionaire inorder to impress. You aren’t a political mover and shaker so don’t try to drop names of big wigs you met during a work event just because you happen to work in Washington D.C. You aren’t a professional athlete so don’t try to go proving how physically fit you are by throwing the heaviest ball in the bowling alley (I do use a 16 pound ball which is the heaviest bowling ball allowed but, you know, whatever).

I’m a movie nerd so I talked about movies. I’m a comic book nerd so I talked about comic book characters. I’m a baseball nerd so I talked about baseball. Rizzo isn’t a big movie fan (she likes them okay but falls asleep a lot during movies), or a comic book fan, or particularly a baseball fan. But she listened and was interested because these were things I love. Rizzo is a teacher nerd so she talked about teaching (and got on a 10 minute rant about using the word “retarted” but we will leave it at that). Rizzo is a fan of the Washington Redskins so she talked about the Redskins. Rizzo is a fan of talking so she talked and talked and talked. And I listened. Not because I know anything about teaching, or care about the Redskins, or even like to talk that much (I’m much happier writing so thank you for reading what I write) but because she was being herself and I found that endlessly attractive.

Be yourself and follow these simple steps to a successful first date and you will never fail. I’m not saying that if you follow these steps on your next first date you will find the love of your life (I did, but, whatever) but I can say with confidence that you will have a good time and at least make a friend. Not everyone is meant to date but if you keep an open mind, listen, and go bowling, everyone can be friends.

Note: No guarantees made during the course of this blog are enforceable in a court of law and the author takes no responsibility for you making a fool of yourself. Unless making a fool of yourself resulted in you coming off as quirky and sweet which in turn resulted in you winning the first date. Under those circumstances your success in dating was entirely attributable to the advice you garnered from reading this blog. You’re welcome.

There may be many first dates but really it only takes one.

There may be many first dates but really it only takes one.

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