#184 - Dating 101

It’s been a while since I’ve written specifically about the basics of dating. More often than not I’m writing about specific aspects of dating and relationships. Every once in a while it’s great to have a refresher on some of the basics of dating.

Dating can be as easy or as difficult as you’d like it to be. Much of it has to do with your attitude and how you handle your experiences. Part of it has to do with how much experience you’ve had at dating. Dating is much like anything else you do; the more you do it, the better you get.

Trial and error is how most of us have learned how to date in our lifetime. Some may have done some reading of popular books to gain a better understanding of the opposite sex and what they might like and respond to. Others may even talk to friends, family, or someone they know that is in a healthy, happy relationship.

Today I’m going to share thoughts, tips, and techniques that if have learned from all of the above in addition to years of experience working with the general public.

Some of these tips may seem fairly obvious to most of us, yet they are missed by way too many people.

Pre-Date Preparation
Men, if you’re going to ask a woman out on a date, make sure you give her plenty of time. This may sound old fashioned, but it is not only gentlemanly, it shows courtesy and thoughtfulness. As a rule of thumb you should call by Wednesday for a date on Saturday.

Know what you are going to wear. Ladies, have a First Date outfit picked out and set aside in your closet. This way, you already know not only what clothes you’re going to wear, but you’ll also know what shoes and what makeup you’re going to wear. This will save you a significant amount of time and stress come date night.

Men, put some thought into what you’re going to wear also. Even if you’re only meeting for coffee or cocktails, dress to impress. Now that doesn’t mean that you’re going to wear a suit and tie especially for a casual meet-and-greet. What it does mean is that you don’t show up in something that look like they just came out of the dirty clothes hamper. If you don’t know how to iron a shirt, get one laundered and pressed. Clean and polish your shoes.

Make sure you brush your teeth, comb your hair, use deodorant, shave and trim hair in all the appropriate places. Carry breath mints with you at all times. Coffee, wine, and garlic breath can be terribly offensive if you are sitting close to each other.

This is also a great time to review texts and emails you’ve sent each other to refresh your memory about what you have already shared. It’s also a good way to make sure your date isn’t changing their story. (If there are inconsistencies in what they’ve shared with you by text or email and what they tell you in person, red flags should be popping up.)

Finally, your pre-date prep should include reviewing The 5 Biggest Dating and Relationship Mistakes and How to Avoid Them.

The Date
Be prepared to be no place else! That means turn of the cell phones…or at least turn them to silent. There is nothing harder to overcome than trying to hold a conversation with someone when they are constantly checking their phone.

Make the first date casual such as coffee or cocktails and go somewhere that is reasonably quiet so you can talk. While a concert, movie, or sporting event can be fun, save that for a date sometime down the road. You want to be somewhere where it’s easy to hear each other talk.

If coffee or cocktails go well, you can always extend the time you spend together. If not, you each go your own way.

Keep the small talk to a minimum. The first date is a time to get to know each other so ask each other questions, but don’t make it an interrogation. There is nothing worse than being bombarded with question after question and feeling like you a suspect in a murder investigation.

The first date is a time to SHARE conversation. That means that both of you should be able to not only ask questions, but to answer them as well. Make sure you’re getting to know your date as well as them getting to know you. DON’T dominate the conversation.

Don’t deflect when you’re asked a question. By deflect I mean turning the question back to them. For example;

Him: What was your favorite vacation?

Her: Great question. What was your favorite vacation?

This is a very simple example and it doesn’t make any difference who is asking, whether it’s him or her. The point is, one is avoiding answering and hiding information. This is a sign of a very guarded person and prevents the other person from getting to know you. It’s extremely hard to get to know someone when they continually deflect or avoid directly answering questions.

Now this doesn’t mean that you have to reveal everything on the first date. If you’re not comfortable answering certain questions, simple say, “I don’t know you well enough to share that information with you at this time.”

Most of all, approach the date with no expectations. It’s so much easier to have fun and enjoy yourself when you don’t walk in with any preconceived ideas about your date.

If you had a good time, shortly after the date is over it’s okay to call or text and say “Thank you. I had a really nice time. I’d like to do this again.” It’s also okay to say “Thank you. It was good to meet you. I didn’t feel the connection I’m looking for so let’s just keep it as friends.”

Be nice. Be classy regardless of the outcome. In virtually every community your reputation precedes you. Women talk to their friends and so do guys. You’ll inevitably cross paths with someone who knows someone who knows you. If you have a crappy reputation, you’ll make dating so much harder on yourself than it needs to be.

Post-Date Analysis
Really? I need to analyze my date?


This is where you can really start to spot any read flags…if you haven’t spotted them already.

Here are a few questions to ask yourself after the date.

  1. Did I feel any chemistry between us?
  2. Did he have a lot of my Must Haves? (You probably won’t know all of them on the first date.)
  3. What, if any, red flags did I see?
  4. Am I attracted to her?
  5. What do we have in common?
  6. Where are we different?
  7. In general does he have a positive attitude?
  8. Can she hold a conversation or did I have to pry answers out of her?
  9. How did he treat other people we came in contact with?

This should get you started. Recognizing all the pros and cons after your date can save you from a lot of potential problems later on.

If your date has potential, keep dating. If not, don’t waste any more of your time or theirs.