The Pitfalls of The Long Weekend Trip With Your Girl

Contemplating a long weekend away with that girl you just met?  Consider the following factors before stepping off that edge, because once you do…there’s no turning back.

Don’t Kid Yourself, It Means A Lot

You may be inventing all the seemingly harmless rationalizations for including that new girl you’ve been dating in your weekend away.  These include but are not limited to:

  1. I already booked the hotel room and travel and it would be fun to have a companion.
  2. She’s cool, I think she’ll be able to enjoy the weekend and not read too much into it.
  3. This will just be a great chance for us to get to know each other.

It may very well turn out to be a fun weekend, but don’t kid yourself…this is a big deal.  She will be telling all her friends about your intended weekend away and expectations will be high.  This puts your growing relationship in a whole new light and it will be evaluated accordingly.

It may not be a big deal to you…but it will be to her.

Ready Yourself For Relationship Hyper Space

Any “slowly getting to know you” that you’ve been doing goes out the window on an extended weekend trip.  You will be with each other 24 hours every day of the trip.  Your buffer zone shrinks to zero (hopefully nothing else will be shrinking as well or that will present a whole new Unfinished Man article).

There will be no “gather yourself” time apart and you’ll see each other at your most raw, bitchy (that includes you) and honest state.  Make no mistake, this can be an awesome and affirming experience with the right person and at the right time in your relationship’s evolution can really seal the deal for both of you.  However, if you jump the gun you could artificially step on a relationship landmine that might have been averted had you waited until you knew this girl a little better.

Can She Hang?

Anyone who has traveled knows that event the most organized itinerary often goes astray.  There are often hiccups, road closings, inclement weather or changes in what you had planned and you have to consider if this girl is going to be able to roll with it.

The more flexible and low maintenance she is, the better your chances of this long weekend being a success.

Try to get a sense of how she likes to travel and how she’s handled travel glitches in the past.  Integrate some seemingly casual questions about previous trips into your conversation.  Try things like:

  1. How do you like to travel typically?  Have an organized plan or just go with the flow?
  2. What was the crappiest place you ever stayed in?
  3. What was the most embarrassing thing that happened to you on a vacation?

Asking questions like this in advance of proposing (pardon the scary term commitment-phobes) a weekend getaway can do wonders to help you gauge if your travel styles align and if this is the right choice.

Try It With A Group The First Time

It’s much easier to transition into traveling with someone you’re interested in by including others in that maiden voyage.  The balance of friends and group activities gives you the flexibility to break away if you want more alone time with her but also allows you the security of a group dynamic if things don’t end up as well as you might’ve hoped.

This approach gives you the added bonus of seeing how she interacts with your friends and your lifestyle in a relatively safe setting.

If planned at the appropriate time, the long weekend away with a woman you are digging can be a game changing experience that transitions a good relationship to a great one.  Proceed with caution and make sure you’re both secure with your intentions before making that next step.




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I work as a full time hair stylist but love writing about life. I hope to become a full time writer one day and spend all my time sharing my experience with you!

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