Avoid Awkward First Dates (And Leave Her Wanting More)

[Clay]

I have a couple of questions:

- During the initial stages of getting to know a new woman and going out on dates, is it best to frame the invitation (from me to her) with an emphasis on she and I getting together (and make the thing we'll actually be doing a mere decoration around us), or make the invitation one emphasizing the activity itself?

That is to say, in your experience, is it better to make it an invitation to spend time together, or to do a particular activity? Hope that makes sense.

- Perhaps an odd question, but one that I've always wondered about. When on a date, say at a lounge for drinks or at a restaurant for dinner, and the woman goes to the restroom, what's the best thing to be doing when she's coming back?

I always find this awkward because you're just sitting there, really with nothing to do, and it feels like I'm powerless in a sense during those moments. I'm sure, having dated a lot yourself, you've developed an approach that works well for you. I'd like to hear what it is.

Thanks a million. Best regards,

[Elliot]

Hello Clay:

Great questions.

The overarching theme here is not to think too hard about any of what you are mentioning here.

If you over analyze, it'll spin yourself into "analysis paralysis" and the resulting insecurity will bury you regardless of which way you go...every time.

To answer your first question, I'd recommending a "both...and" approach instead of an "either...or".

In other words, it doesn't have to be positioned as either something cool to do or a chance to hang out with a cool guy like you.

It's kind of like asking if you should press the clutch or shift the gears when driving. See what I mean?

The premise is that because you're such an amazing guy, of course you're going to plan amazing dates.

And yet, said "amazing date" doesn't have to be a huge, financially draining production of an event, either.

In fact, the likelihood is that a natural setting doing something normal people do anyway will be much more amenable to getting to know each other more effectively anyway.

Try something like: "Hey, I'm planning to go to the Bombay or Pier One to pick out a new lamp for the living room. I could use a woman's insight. How about you join me?"

It doesn't really matter where you are going and what for, as long as it isn't too downscale (e.g. to the Circle K...) or creepy (...for some Preparation H).

Of course, it goes without saying that avoiding lounges and restaurants altogether obviates your second question entirely.

There's no such thing as "waiting around doing nothing" in the example I mentioned above.

In fact, I'd pick her out something completely silly that you'd tell her with a straight face is "perfect for her" when she returned from the ladies room. Ha!

But if you do end up finding yourself alone at the table in a restaurant twiddling your thumbs anyway, here are several ideas:


1) 20/20 foresight says to plan early dates at fun, easygoing places. Lots of guys--especially ones who haven't figured out how women really think yet--plan expensive first dates at "romantic" restaurants.

Your example is but one of myriad reasons why high-pressure first dates with a serious tone are a rotten idea.

It's all about finding out whether you genuinely get along with a woman or not during the early stages, not about attempting to manufacture "romance" where none exists (yet).

That said, I'm not going to at all discount the raw horsepower of a dimly-lit romantic hideaway of a place when it comes to setting the mood, but this is about timing. And first dates especially are rarely the best times for such.

Instead, pick a place that has big TVs, a cool jazz band playing or (especially) something interactive going on like Buzztime trivia.

Then, when she excuses herself for a few minutes you're otherwise occupied...and naturally so.


2) Anticipating the potential awkwardness of the situation you described, you may also pay careful attention to positioning.

Maybe sit at the bar instead of a big old sloppy booth. That way, there's social interactivity built in.


3) If you're tell the waiter or waitress you aren't bailing on check, you can use the opportunity to excuse yourself from the table for a health break also.

Make sure she didn't leave valuables behind if you do this (and don't take her purse with you if she left it there, either!)


4) Or, you could...(wait for it)...stop giving a rat's behind how you look.

Believe me, the Awkward Turtles are likely swimming around in her own aquarium simply because she felt a little silly excusing herself to begin with (unless...uh...she did so specifically to plan the dreaded "escape call", but you'll find out the answer to that question shortly thereafter anyway).

Seriously, though. Stay casual and relaxed. "Powerlessness" in such an instance is simply "insecurity" in disguise. Be patient, and if possible don't make it blatantly obvious that you're scoping out the "scenery" elsewhere.

Remember where the conversation left off, and resume it when she returns as if nothing happened.

Be in control. Be a man who is comfortable in his own skin.

Bodily functions happen. You don't look dumb because she needed a break.

Your mental state will lead hers naturally. And if you still need a visualization, consider how this would go if the shoe was on the other foot.

Would you return from the men's room to find her sitting there casually waiting and think, "Wow, she looks like a total idiot sitting there by herself...no second date for her."

Of course not, man. It's all part of being a human being.

Thanks again for the outstanding questions.

[Clay]

Thanks for your advice Elliot

[VeronaRodriguez]

Nice tips there Elliot!