Putting the CON in Confidence… Part I

I love my coffee

When Amy and I are asked to name the one quality that women find most attractive in a man, the answer is easy: CONFIDENCE. We hear it every day, and while it’s true that some guys can seem a little bit too confident, confidence is a lot like money; it’s hard to tell when you have too much of it, but it’s very, very obvious when you don’t have enough.

Confidence is absolutely essential for converting a first date into something more, and eventually ending up in a relationship; after all, if you don’t believe that a particular woman should be interested in dating you, then why should she be? And how are you ever going to convince her that you’re the right guy if you can’t even convince yourself? Given that we aren’t all 6’5” with a cleft chin, a full head of hair, and huge biceps, it can be easy to doubt yourself or be anxious on a first date. Thankfully, a little bit of confidence is something a guy can fake pretty easily (Do you hear that, ladies? You aren’t the only ones who can fake things.). And for a guy who’s low on self-esteem, even faking just a little bit of confidence can go a long way.

1. Before you pick up the phone, have a plan.

Under no circumstances should you ever call a woman for a first date and say “What would you like to do?” As a man who has spent most of his life dealing with “complicated” women, I can tell you that this is a huge mistake. To get the upper hand (and earn some respect at the very beginning of your relationship) only present her with a series of Yes or No questions. And do them in order of Day, Time, Place, and Transportation. For example:

“Are you Free on Saturday?” No? “How about Sunday?” No? “Can you be free for dinner on Friday?” Once you get a yes, IMMEDIATELY move on to times. “Does 6:30 work for you?” No? “How is 7:30?” No? “Great, I’ll make a reservation for 8pm.” Then move on to “Do you like Indian?” or “I was thinking of this Burmese place” or “I thought we could go to a bistro I like in Saratoga.” Be sure to have three or four different options picked out in advance, and once you get a Yes, MOVE ON. “May I pick you up?” No? “I’ll see you there. I’m looking forward to it. Feel free to text me if anything changes.” And then HANG UP THE PHONE.

Do not ask “What times works for you?” DO NOT do that. If you do, she will likely spend several minutes telling you why all of the other times do not work. You will feel beaten by this. You will be tired. We do not want that. And do not ask “What kind of food do you like?” Do not do that. Because most women will tell you what they don’t like instead of what they do. Even if she started with something like “I love Thai” you will end up hearing a story about food poisoning or a bad date or a cockroach that she encountered at a Vietnamese place with bad lighting on the outskirts of Boston that she mistakenly frequented during her first year of grad school. Ten years ago. And you will forget where you are in the entire date planning process. See? You probably forgot where we were in this lesson, and I only distracted you from the path for just one sentence.

It is really key that you do not open any windows into her past in this initial phone call. Remember that this woman is interested in dating a gentleman – and you might be that gentleman – so take a firm hold of the conversation, and make sure that you only open the door that leads to her future.

If you’re new to the area (or new to dating) or really want to make a great impression, Amy and I will happily give you recommendations if you ask. And we can certainly make you aware of any dietary restrictions or allergies you should consider. Make a checklist if you need to, but go into the call with clear goals and objectives, namely a day and time that work for you, a place you want to eat, and clarity on how she’ll get there. You’ll be off to a good start. And believe it or not, she’ll be glad you took the lead.

Next time, more tips on how to fake it… for when you’re actually on the date.

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