[X&Y] Avoiding Awkward First Dates (Reader Question)
Published: Wed, 03/19/25
Updated: Wed, 03/19/25
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IN THIS EDITION: A reader wonders what exactly to do during
potentially awkward moments when you're out with a woman.=====
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READER QUESTION: AVOIDING AWKWARD FIRST DATES
Hi Scot,
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.
Next, this is 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,
Isaac (Australia)
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Hello Isaac:
Great questions, man. Probably the best I've gotten all week.
The overarching theme here is not to think too hard about ANY of
what you are mentioning here.
If you over analyze this sort of stuff, it'll spin you into
"analysis paralysis" and the resulting insecurity will bury you
regardless of which way you go...every time.
That said, I do have some pragmatic answers to your questions.
In response to your first, 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 pedal OR
shift the gears when driving. See what I mean?
And you don't have to make the discussion into a big, nerve-
wracking deal.
The more laid back and matter-of-fact you are about the whole idea,
the more likely she'll be to follow suit. That's a good thing.
For what it's worth, the actual plans you make don't exactly have
to be a huge production, either.
In fact, the likelihood is that a relaxed setting doing something
that normal people do anyway will be much more amenable to getting
to know each other more effectively anyway.
Be sure to position it as a suggestion rather than a question, too.
Try something like: "You know what? 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. You should 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
(e.g. to the drug store 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 such
"relaxed settings" as the example I mentioned above.
In fact, while she's in the ladies' room, I'd pick her out something
completely silly that you'd tell her with a straight face is
"perfect for her" when she returned. 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 countless 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.
It's that or play with your smartphone, I guess. But you'll have to
trust yourself to put it down when she returns.
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. Perceived
"powerlessness" in such an instance is simply "insecurity" in
disguise.
Bodily functions happen. You don't look dumb because she needed a
break. Your mental state will lead hers naturally, so be patient
and relax
If there are any other good looking women around, don't make it
blatantly obvious that you're scoping out the "scenery" elsewhere
while she's gone.
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.
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. So rest assured she's not thinking like
that either.
Thanks again for the outstanding questions.
If you think about it, you can take everything I've just shared
with you and apply it to ANY potentially awkward situation on a
first or second date.
For example, everyone spills coffee or trips over the edge of
the carpet at some point in his or her life. Make light of such
a situation if it happens to either of you, and get over yourself.
=====
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