The first trip away with a new love-interest is an exciting thought, but how do you know if you are really ready to go away together? Here’s a recent question from a single girl who is contemplating a trip away with her new beau…
I’ve been dating a guy for a few months and recently he’s asked me to go on a trip with him. We’ve never spent several days together all at once without a break and have never taken any trips together. I really want to go, but I don’t want anything to go wrong to ruin our relationship. If we decide to go on our 1st trip together, do you have any tips for making sure it goes well? Do you think it’s too soon to go on a trip together?
Though I wouldn’t discourage you from going on a trip with your love-interest, I would suggest that you prepare yourself for potential things that could happen or that may be expected of you while traveling with your new guy. Three things you should make sure you’re prepared for are the sleeping arrangements, the costs associated with the trip, and discussing what type of trip it’s going to be for the two of you. Let’s talk specifics….
1. Being okay with the sleeping arrangements
Though staying overnight with someone doesn’t automatically mean there will be sex, there is an assumption there that you are prepared to share some level of intimacy. Especially if you two haven’t been intimate yet, you should seriously think about this. You will be sleeping in the same room together, and quite possibly the same bed, so just imagine how uncomfortable it could be to be in close quarters with someone who’s not on the same page. It is never okay for someone to force you to do something you don’t want to do, but you also shouldn’t put yourself in an uncomfortable situation if you can avoid it. If you aren’t okay with all of this, you may want to consider postponing the trip until you’ve gotten to know your guy a little better.
2. Be clear about who’s paying (or who’s not paying)
Generally if you’re being invited somewhere, the person inviting you should be prepared to pay for the majority, if not all of the trip, but you also should be prepared to make a financial contribution while away. If you would be in any way offended by paying for part of the trip, then you shouldn’t go. Never make assumptions about money in these kinds of situations. Always have cash in case things don’t go as planned and so you’re not left in an uncomfortable situation far from home.
3. Discussing the vacation (sporty, relaxed, touristy, romantic, partying)
Is your love-interest planning a ski trip, but you’re not into skiing? Does he want to go to a spring break destination, but you’re not a big partier? Are you going to be sticking to a strict schedule or will the trip be all about spontaneity? Make sure you know what kind of trip he is interested in before you commit. Not everyone has the same idea of what constitutes a fun vacation. Figure out what he’s planning and if you’re not on the same page, suggest adding another option to the agenda.
Before you commit to the trip, start a conversation with your guy about his plans. It’s always best to talk specifics, but even if you don’t cover all the important topics before you go, make sure to talk about the things that are most important to you. If there is anything you would be uncomfortable with, make it known and discuss it to find a solution. Through this conversation you should find out if you are truly ready for a trip away with your new guy (and indirectly find out if he’s really ready for a trip away with you).
Remember, a trip with a love-interest can be super fun as long as the two of you are on the same page. To get on the same page, have the important conversations now, so you can focus on fun while you’re away!
Good luck and bon voyage!
Hugs,
The Dating Advice Girl





























