This Monday I’m tackling a topic that I’m inspired by – mostly because I just came back from vacation with my significant other. What a glorious thing! So, that gives me the right to give relationship advice and it has me wondering, at what point do you take the leap and go on an overnight or weekend trip with that special someone?

The first thing you should ask yourself is – do I feel comfortable doing this?

Do you feel like you know that person well enough to spend an extended period of time with them? Do you know they’re not a serial killer and won’t take you into the woods and leave you for dead? Joking aside, feeling comfortable is important. I know people are always saying to “do things out of your comfort zone” which is valid, and great and awesome to do! But, in this case, don’t go totally out of your comfort zone for a date – you can always do a more simple date and not go on vacation at all! Then you can wait until you DO feel comfortable.

So, let’s say you’ve decided to go – now you probably have a bunch of questions racing through your mind, like will we have enough to talk about? Will it be weird to spend that much time together? Will we get sick of one another? Well, no better way to find out than to just GO FOR IT! Why not? The worst that happens is you might realize the two of you aren’t meant to be together. At least it’s a learning experience and maybe you’ll even have a funny story to tell!

Believe me I’ve got one of those – shout out to the guy I went to ZBT formal with freshman year of college. Yes, I did go on a blind date weekend getaway – which I do NOT recommend under any circumstances!! Don’t do it! Speaking from experience here people.

A few more things you might want to consider:

1. Have you slept in the same bed with this person? You might want to do that first… 

2. Have you had sex with this person? Not totally important, but it might be a lot to go on a weekend date and have not sealed the deal yet.

3. Who’s paying? (Always good to know ahead of time – are they expecting you to split the bill?)

Most importantly, do what makes you feel comfortable and happy!

Are you looking to find that person to go on vacation with? Let me help you find! Sign up for your free consultation here.