Ok, this random. I just got divorced, and i have booked a Non-Refundable 10 Night Stay (5 Star, All Inclusive) in Cabo. Would it be wrong to ask a potential date to go with me ? I am going either way, but it would be nice if i can ask someone to date me and we can go together. How can I find someone ?

Thoughts ?

p.s I am not ugly or crazy…

18 comments
  1. That would be a great date but it feels too much for a first one. If you guys don’t click it will just be an awkward 10 night vacation and I don’t think you want that. Just my opinion.

  2. Pack your sense of humor and let’s see if we can survive each other! 🌍✈️

  3. Just get on the apps when you’re there, it’s not hard to meet people when traveling.

  4. Just go with a friend and enjoy some low maintenance time away. You’ll have a wingman and have fun in Cabo.

  5. i’d recommend using this trip as a time to connect with yourself for the first few days. unplug, unwind, and relax. keep you phone in the dresser

    after that, i would encourage you to go out to the local bars/clubs and just let the night unfold. i did this in hawaii, and met a lovely woman. we met at the bar, went to Safeway, got some snacks, chilled by this lake, made out a little bit, and i dropped her off at home. one of the best nights of my life

  6. Are you male or female? I’m okay with either but we need to establish boundaries.

    If you’re a male: let fucking go bro. We’re going to plow all sorts of ass, just not each others… ill willingly take the fold out.

    If youre a female: I sleep on the side of the bed closest to the door. (This is my only demand) anything else goes.

    My offer has been made. Do with it as you please.

  7. My first date with my ex was similar.
    We had like a free trip and went as friends.
    Though we were already long time friends.
    And romantic feelings happened on the trip.

    I would really get to know them enough though to have that kind of trust.

    Or take a girlfriend is a better idea.

  8. Happened to me once with someone whom i was seeing for the second time and it was a 3 night trip – 3,5-4 hr drive away. We had met through bumble and she spent the first night at my place. So second time, 2-3 days after the intial meeting, we were on the road. I ended up cutting the holiday short on the second night, couldnt stand her one more day ; left at 07.00am on the third days dawn. I couldnt leave her so it was even more awkward. I was going 220 km/hr so the return took me 2,5 hrs ; didnt even give a toilet break. Trust me, it is increadibly risky, dont do it 🙂

  9. Pack your bags, my friend! Let’s embark on this adventure together!

  10. I did this once. We’d only been on a couple dates, but we had a pretty good sense of each other and we felt safe about it. It worked out fine, notwithstanding the fact that I was still very hung up on the girl I’d just broken up with (and with whom I had planned to go). She (my new date) was aware of the situation and decided to take a chance on it anyway.

    Went to Hawaii for five days and shared a really nice condo right on the water, same bed and all.

    We actually flipped a coin when deciding.

  11. Bring yourself or a friend! I would go it alone, honestly. I definitely wouldn’t lead with that when looking for a date, as it will be more about the trip then you. If you’ve been seeing someone for a bit, already, it might be jumping the gun but you never know how they feel about it? Nothing would be worse than a trip ruined by a relative stranger who turns out to be horrible to travel with, imho.

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