First Dates-What Do I Do? Where Do I Take Her?

First dates can be the bane of man’s existence. The anxiety of not knowing if she will like you, not knowing where to take her, and wondering when and if you should go in for the kiss. How about we wipe the slate clean of all of the aforementioned first date related cliches and re-frame the entire experience? Sounds like a good idea right!?

First off, you should not be going on a first date if you do not already have an inclination that there is at least a minimal amount of chemistry between the two of you. In fact, what you should be doing is setting up your first time hanging out(yes I called it “hanging out” instead of a date) such that you both cannot wait to see each other. This means you had a great time meeting each other initially whether it was out at a bar, in the grocery store, online, etc. You have continued to talk, text, chat, Skype, messenger pigeon, and on and on before you even setup your first official time hanging out. This way you already know some of each other’s preferences thus eliminating ending up at the local crab house when she’s allergic to shellfish. This will also ensure you have plenty more to talk about while on the date. There should be almost no nervousness on the first date. The goal is to fall in “lock step” connection with one another. Think of this as effortless flow. You are both totally in the moment and absorbed by one another’s company.

My favorite “first dates” are those in which you hangout in a low key, laid back environment. This way you two feel like you are hanging out instead of on some sort of formal Q&A session. Scratch taking her to dinner here, unless its to some sort of cool interactive dinner show or something along those lines. The more formal your “first date” the more pressure you will both feel to impress. I am also not an advocate for buying a woman flowers on a first date. I think it’s too formal and can often times put too much pressure on the situation. I believe in starting out on neutral ground. No gifts or anything that says you are trying to win her over. And the key to any good first time hanging out is to simply connect with one another and have a good time. Hanging out for a few drinks at the local bar is always a great “first date.” Simple, fun, involves the world’s oldest “social lubricant,” and if it gets awkward it’s easy to end the date since there are no time constraints of waiting for your food or for a movie to end.

My favorite “first dates” are ones in which one or both parties show their personality in their selected location choice. Chelsea and I went for Kava(her idea), played darts, and drew funny pictures with crayons in a coloring book on our first date then had a few drinks at an Irish Pub. We had a blast and it was as low key as it gets. Please note following Kava with alcohol is not a good idea ha! Anything interactive is always great for a first time hanging out. Playing mini golf, bowling, pool, darts, etc is great because you are moving, you are physical, you can still talk and get to know each other. The physical activity involved can also help to calm the nerves. Chelsea and I actually referred to our dates as “adventures.” We made a game out of it. She chose the Kava adventure and for our second adventure I took her to a gun range.

As for the kiss…I am ALWAYS an advocate for going in for the kiss. It’s important to escalate things physically if the date is going well. Otherwise you run the risk of entering into the dreaded friend zone and/or being labeled as a “sweet” and “nice” guy. These two terms are code for “she’s just not that into you.” Sweet and nice don’t spark attraction. Keep in mind that sparking attraction during your first time hanging out can be the difference to her “allowing” you to kiss her and her practically “begging” you to kiss her. Let me give you an example of how to set the stage on your date. You are still going to be “nice” and “sweet” in your actions but you are going to deliver these actions with attractive swagger.

When you pick her up, say something like this, “You look lovely ______. Now before we begin our (adventure, date, hanging out, or whatever you want to call it) I need to lay out the ground rules. I expect you to open all doors for me, pay for anything that costs money, let me beat you in any games that we play so as not to affect my ego, and most importantly I am a born again virgin so don’t even attempt to whoo me with a goodnight kiss.” Say this with a straight face until you get a reaction and then smile to let her know you are kidding. She should know you are kidding before you finish the sentence if you have already had a good joking dialogue with her leading up to your first adventure. Remember, keep things light, breezy, and fun in the beginning. Light, Breezy, and fun is attractive. Serious and setting expectations of what your relationship should be or will become is not attractive. This line also lets her know in a funny way that you are in fact a gentleman because you know all of the things that are expected of you as a man. This type of line can have the affect of making her want to go against the grain also. She may actually step in front of you at the first place you go and open the door for you with a big smile on her face. If she does, guess what, it’s on baby! It shows that she is totally comfortable with you and at least minimally attracted to you. Keep the light, breezy, and fun attitude up and she’ll be planting her lips on yours before you can even begin to think let alone say good night to her!


I hate the word DATE!!!!! People often stress about going on dates because it usually falls under the circumstances of the two people not knowing each other at all! Naturally you would think it would make perfect sense to take that “stranger” out to dinner and play 21 questions, but there is a better way for you to beat those butterflies and save some $$. I always here my girlfriends saying “Oh I just want a guy to take me out to this place and wine and dine me.” When they do go on that type of date, there is no connection at all and they end up texting me looking for excuses to leave. That’s because first of all they were going to dinner just to be taken out and secondly they barely new the guy but had high hopes of drinking a bottle of wine and having a drunk connection. Girls like this are a waste of time and money, but how were you supposed to know that? You asked her out on a date and she said yes and made a recommendation on where to eat. You find it hard to hold a conversation so you both continue to order drinks that you end up paying for. AVOID THIS!!!!!!!!!!!!!!!!!!!!! Don’t ask every girl you think you have a connection with out to dinner. Dinner is so cliche and most times awkward. If you are interested in a girl and you think you have a connection with her be adventurous! You don’t have to be crazy like Steve and I but do something different. The girl will automatically be shocked that you didn’t ask her to dinner and might even be excited to try something new with you. Some recommendations that I would enjoy on a first date would be bowling, going to a pool hall and being interactive playing pool or darts, wine on the beach etc…. Find out things she has never tried before or look for things going on in your local area such as fairs, pottery painting, music events, or wine tastings. Shy? A change of atmosphere will give you something to talk about!! You don’t need to take a woman out and spend a lot of money, there are so many other things you can do that are just as fun and memorable than eating a lobster that you think is impressing her. If you feel the need to impress a girl something isn’t right. Are you compensating for something you don’t have? Are you insecure? Are you a jealous guy and feel the need to let her know that you have money so she’ll stay interested? All of these are common traits but if you find that you have one there is something you need to change. You will find a girl or two who would rather go out to dinner and be boring but is that someone you really want to pursue?A plain Jane? YAWNNNNNNN!!!!!!!!!!!!! When you go on one of your adventures and assuming all goes well, find out what she likes to eat and instead of taking her out to dinner you can cook for her or cook together!


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