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Home Love & Relationship

Are You Ready To Go On A Holiday With Your Boyfriend, Or Is It Too Soon?

by Pooja Sheth
May 29, 2025
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Congratulations ladies, you have made it well and far with your boyfriend, steady enough to plan the… next step! Being at the point you are now in your relationship, it’s hard not to think about what the next chapter might be looking like for the both of you.  But, are you afraid to bring this up as it might freak your partner up, or you strongly feel that your relationship is not at the point you want it to be? If your feelings are wedged, it’s best to give your relationship a little more time before taking on the huge step.

On the flipside, if you’re ecstatic and ready to plunge to the next phase with your boyfriend, a holiday is the best way to move forward. A holiday with your boyfriend is not as daunting as a proposal, but it’s a subtle hint that both of you want to further explore the beautiful relationship and see more of each other, in a whole new exciting level. When you’re spending the entire day and night together doing different activities, you’re going to know each other’s intricate habits, likes, dislikes and behaviour in a magnified level. Trust us, it’s a different ball game as compared to going for date nights.

No doubt taking a trip with your boyfriend will further strengthen and deepen your relationship. It can also highlight any red flags that you need to know before both of you get too invested. So, before you start booking your private pool villa, you might want to keep these pointers in mind.

Plan fun activities together

Pinterest

The whole point of this trip is to spend quality time together. But that doesn’t mean you can’t plan some exciting activities, right? Plan out a rough itinerary on what you guys plan to do during your vacation. If both of you are adrenaline junkies, then try to do something out of the norm like scuba diving, bungee jumping, or other sporting activities that’s made available. If you’re clueless, avoid getting into a boring situation. A quick fix would be to stay in, order in and watch a romantic movie together. It always works!

Make sure the trip is not too short but not too long either

Men’s Health

You do not want the vacation to be too short feeling incomplete, nor too long or else boredom might creep in. After all, you are vacationing and there’s so much you can do to enjoy. If it gets dragged on too long, the tone of the trip might get monotonous. So plan a trip for a couple of days, and again, having an itinerary is crucial to avoid any disappointments.

Try to squeeze in some alone time as well…it’s important!

Pinterest

We know the whole point of the trip is to spend as much time together, but know that having some time alone for yourself is also key. You can do this by going for a quick walk in the morning while your partner is still asleep, reading a book by the pool while your boyfriend sweats it out in the gym, start off having breakfast alone and then accompanied by your partner, or any other ways you can slot some time for both of you to recoup.

Watch out for those annoying habits — both his and yours!

via GIPHY

When you’re going to spend the whole day and night together, your habits that have been concealed all the while surface up, and it’s best to watch out on them. You do not want to weird out your boyfriend after he gets a peek into your habits. You still want to impress your better half so if you’re a messy person, try to keep the place clean and your clothes organized. During the trip, you will be seeing a lot more of each other, so fine tune your habits because you do not want any of you raising eyebrows thinking “what did I get myself into”.

This is the ultimate test of your comfort level with each other…so be prepared

via GIPHY

Oh yeah! Want to get to know how clean, hygienic, disciplined and annoying your better half can be? Stay with them! Staying together unlocks every private doors, including your sleeping habits, bathroom hygiene and even time management. You want to show the best you have to offer despite sharing ultimate closeness. It can be weird to pee or do your business knowing your boyfriend’s sitting out there and can probably hear you. But this is what the real test is…you’re both grown adults and you need to be comfortable enough with each other to get past these little insecurities.

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