Dating 911! First Date: The Most Dangerous Game

Welcome back to the series which purports to tell it like it isnt. We abuse you any notions of truth and beauty and leave you wandering out there in the wilderness, unsure of where to go or to whom to turn. Never mind that now. We actually may help you with a way out of the wilderness of dating as we venture back into the ritual which is known as the first date. Its the second of our three-part series covering the scary ritual, otherwise known as the first date. Welcome to Dating 911! First Date: The Most Dangerous Game.

When we last left you hanging, we discussed all the things you needed to know before you went on the first date. And while much of our focus in dating covers what other people should do or look like, we inverted the focus. Instead of focusing on what the other person was like, we wanted you to focus on what mattered to you most. And then we told you to make sure you communicated your thoughts and desires to the person you were going to go out on the first date with.

The reason we did this was far too often we leave so many things up to chance. And its not that we always have the right attitude or desires going into a first date. When we do not communicate properly with our date, its no wonder we have so many first date disasters. Secondarily, so much of our dating experience comes down to pain avoidance instead of properly seeking someone out. Whether its because we hate the way we have been treated or received treatment, we avoid hardship. Maybe its a condition of human existence. We dont like to suffer or to feel like we make others suffer. But avoiding it in dating tends to produce more of it in the long run.

First Date: The Most Dangerous Game

So now that we have communicated with our date our own expectations, and hopefully they have done the same with us, its time for the dreaded first date. We must actually put ourselves out there and be ready for everything. This means, hopefully, we have the kind of outfit which is appropriate to the date we are on. For the females out there, we have put on the kind of makeup which would go well with the date. Obviously, if they take you to the theater (stage not the screen), it would be different than a day out mini-golfing and eating pizza with regards to makeup. You have done all the preparations for your first venture out there. Take a deep breath, look out to the edge of that dating cliff, and jump.

People tend to look at dating sort of like a safari like theyre trying to land the trophy. Henry Cloud

Dating 911! Taking The Leap of Dating Faith

Prep work is essential to first dating success. But beyond the prep work, one must make sure to do things on the first date which will lead to the success or utter failure it will become. Dont think of failure as a failure though. Think of it as successfully weeding out a potential disaster in the future. So as you keep these things in mind, remember its an adventure, with pitfalls and lions out to eat you at every turn. It truly is, the most dangerous game.

First Date Rules

First Date Rule #1: Arrive On Time Or Slightly Early

I do believe that men and women think very differently with this. Most men dont have the same negative reaction to the lateness of their date women would have. If a man arrives late, it says something about his character. If a woman arrives late, it says something about their makeup routine. And no man would complain about the woman he dates wanting to look good for him. So we have almost this double standard. But I want to say this double standard needs to become a single one. Not simply because Im a male. But because of the pressure. This adds pressure on the first date, as a whole.

This is the first date. You two have never met each other, and are looking to feel one another out. Every second you have together counts. You do not know whats going on in the mind of your date. What if they have a child and need to get back to them? If they planned two hours, assume you have two hours of worry-free dating. Two hours which you have cut 15 to 30 minutes from. Now maybe you can have a good date in an hour and 45 minutes. Nothing says you cannot. But if you have put the other person under time constraints you have made your dating partner violate the predating caution to come in with the right frame of mind.

Your date feels the need to look at his watch, which he wouldnt have beforehand. And you keep wondering what he needs to get back to which would be solved by just coming back late 15 minutes. Yes, you know he has a kid. But how would 15 minutes make a difference? It does. If only for peace of mind, it does. You want them to have peace of mind with you. So prepare to get there early, even if you arrive on time. It can make all the difference.

First Date: The Most Dangerous Game

First Date Rule #2: Greet The Person

Hopefully, you have been smart. You have taken the time to discuss what you like and appreciate on a first date. If you are dating an Italian, they might have told you greetings for them might be a kiss on the cheek. Whatever the greeting is, hopefully, you expect the greeting you get because you have talked about it beforehand.

The problem becomes when you have not spoken to one another before the date about the kind of greeting you get. You move toward one another and then you pause for a moment, unsure of what will come next. If you havent discussed the fact you dont like hugs and you get one, you have no one to blame but yourself. If you love hugs and they play it safe giving you a handshake, you cannot be disappointed by what you get.

My recommendation when you havent spoken beforehand? Give them the side hug. Its not quite straight forward and doesnt invade the same kind of personal space than the face to face hug. It also is a little more intimate than the handshake. This means you are expressing a desire to be intimate, even if you are being cautious about intimacy.

My only rule of thumb about first meets is you dont jump into kissing the person. Unless you kiss the cheek and have expressed this is your greeting. OR you two have moved past the hugging stage before a first date. This means your dating relationship will be fraught with other issues but at least you cannot blame the kiss for your dating failure.

First Date: The Most Dangerous Game

First Date Rule #3: Talk To The Person

I know it sounds crazy one would have to mention this for a date. But you would be surprised how many people say very little on the first date about themselves or anyone else. I have had way too many dates where the other person barely says a whisper from the other end. It didnt matter how many questions I would ask or what was going on. They sat and stared at me. A highly uncomfortable feeling for a first date.

If your nerves get the best of you on a regular basis for first dates, get one of those silly card games which encourage you to talk and bring it with you. It might be an odd first date. But odd isnt bad. If they like you, they will call you unique. This means you stand out to them. No one complains about someone who stands out.

First Date Rule #4: Ask Questions Of The Other Person

Hopefully, this is a two-way street. But you should be asking questions that are meaningful to both of you. Dont make it an interview-style set of questions. Make it about something you have learned about them but would like to dig deeper on. So if the person is interested in computer programming for some company, investigate. Learn about the company. Ask some questions about the company or what they love about it. Prove you have learned something about them and show who they are is meaningful to you. Even if you end up as friends, this will solidify a friendship and mutual care and concern. Remember, the first date means digging to get to know the other person more. It shouldnt be small talk.

First Date Rule #5: Be Ready For Answering An Uncomfortable Question

Ultimately, when you get to be with this other person, you need to express a willingness to be open. If they start asking for street address it might be a bit much. On the other hand, if they ask about why you didnt finish school, or why you ended up as a podcaster instead of a lawyer, you need to have something to say. And even if the answer takes you into uncomfortable territory, be ready to answer just the same. You might have to bring up an ex or two, but be ready to answer the question. Which brings us to the next rule.

First Date Rule #6: Do Not Spend The Entire Date Discussing Exs (Or Your Child(ren))

I will admit wholeheartedly I have the problem with this the most. When you have a daughter and the conversation leads to discussing her, how do you not bring up your ex? Just the fact you have an ex and a schedule with your daughter makes talking about the ex and the schedule almost a necessity. Nevertheless, try to stay away from the ex on the first date as much as possible. The first date should be about the two of you. If it works out, there will be plenty of time where the ex will end up coming up. Instead, talk about the things you enjoy, which are meaningful to you.

A side caveat, which also becomes difficult is to avoid spending the date talking about your child as well. This one is almost harder. Because your child is an essential part of your life. Anyone who cannot see that will not work for you. On the other hand, spending the whole first date talking about them sends you on the same path as talking about the ex. And it might force you to bring up your ex a time or two. Sure, answer a question or two about your child, but try to make the date about the two of you.

First Date Rule #7 Closing The Date Out

This could be a category unto itself as there are so many moving components here. Some will depend on how well you discussed this beforehand. And some will depend on how well the date went while you are there. If you have done all the right steps about discussions beforehand, everything else will be easier. On the other hand, you still have to be able to read the person and situation. And sometimes even reading the situation becomes difficult. So lets take them all one by one as best we can.

First Date: The Most Dangerous Game

  • The Walk Back

Obviously, if this was the worst date ever and you are the woman, avoid having them come back to you with your car at all costs. Which means tell them. You will walk back on your own. If you got a ride to the date on a first date (not my recommendation) try to be as cool as possible to everything. If you are the man, Id be polite and walk them back to the car.

Offer to walk them back at the very least. And if you drove them, do not ditch them, no matter how bad a date it was. Do what feels appropriate. But be a gentleman no matter what. If it was an amazing date, expect the person to want to carry on the date as long as possible. Invite them back to wherever your date ends, but not into a house if they drove you, and not into the car if you drove yourself.

  • The Final Goodnight

Hopefully, you have discussed what you expect this looks like. If you havent, expect the unexpected. And whats worse, expect it to color the entirety of your date. Which is why I say work this out beforehand. If you do anything else you are playing with fire. Ultimately it comes down to what you are comfortable with, and what the other person is comfortable with. For bad dates, always extend the hand. Im not saying the other person wont try something. But the hand puts a distance between you and will keep the person at arms length. Its safety for a woman and less confusion for a man.

If the date went well, go with what you said you were comfortable with. For the woman, if you really like the guy but you arent sure about the kiss, then put one hand up and one hand around the gentleman and move your head to the side. Then make it a strong hug. The hand up and the hug will be mixed signals. But the strong hug and finally moving your other hand around the guy will give them the impression you liked them. If you are ok with the kiss, make sure you have been at least a little touchy-feely if not throughout the date then definitely at the end of the date. Grab his hand as he walks you to the car or your door. Touch him in some way which expresses approval and interest. This makes sure the unsure guy gets the signal.

For the guy, do your best to read the signals. If the date went well, touching or holding their hands helps to express interest. Dont overdo it. Be sure to show respect. And then go with what was discussed if there was a specific discussion. If it was play it by ear, go with what feels right and from whatever signals you picked up from them. But better to err on the side of caution and then realize the woman expected more. If you go for the hug and realize they were going in for a kiss, easier to try to move in for the kiss afterward.

  • Final Words

Your night could end with a kiss. And maybe that says enough. If you are interested, it better be enough. On the other hand, when lesser goodbyes have been expressed, sometimes its hard to pick up on what those mean. So all I can say here is be honest. If you are still making up your mind about a guy, which is probably the case, invite them to call again, or do something again later.

If you are interested, dont make it an invitation, make it a direction. Instead of saying maybe call me again say call me. Whatever you do, if you arent interested dont make it an invitation or a direction. Say thank you and end it there. I would argue its even better to say thank you but no thank you to a future date immediately. Mess around at all, and it wont be better for anyone later. Not even the person who spared the feelings.

Wrapping Up The Most Dangerous Game

It seems like there is a ton to remember, which in truth there is. One will get better with certain things over time. And certain things will be nearly impossible to get better at. After all, everyone gives off different body signals. Which is why sometimes its better to be obvious. Either way, Dating is a game played by amateurs. The professionals have already won and are off the game board. And lucky them indeed. Now if only we could be so lucky.


First Date: The Most Dangerous Game

Continue The Conversation

What is your craziest first date experience? If you had one thing to tell yourself before you started dating, what would it be? And what first date rule would be the hardest to follow?

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Until next time, this is me signing off.

David Elliott, The Single Dads Guide to Life

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