[uberstuber]

I haven't been traveling quite as long as GP but here's my two cents. Even as an introvert getting social interaction improves travel so much.

In a new city try to find a 'social hostel' (not a party hostel, unless that's your thing) with organized walking/food tours. Go on said tours and chat with everyone. After the tour see if anyone wants to get dinner/drinks/sight-see together.

Basically everyone in common areas at a hostel will be open to conversation at least. Be the initiator, chat with people, organize a group to go get dinner, etc.

If you aren't good at being the initiator, try to find someone who is and befriend them. Add people on whatsapp/messenger and setup a hostel group chat.

Befriend people who are also traveling longer term, they're usually more open to change plans a bit.

Socializing takes more effort and most relationships will be fleeting, that's the nature of the beast. But nothing makes a trip like organizing a small group of friends to travel together to a few different cities. You can create much stronger bonds and even some life-long friends.

[tokyodude]

This is probably my prejudice but 'social hostel' to me suggests under 30yrs old. I find at my age while I have no trouble hanging out with people in their 20s there are issues. For example having to eat at the cheapest places because none of them are financially secure yet. Or listening to their 20 something issues and feeling far outside of that time. There's also probably getting use to more comfort as in the comfort of a nice private room with a nice bed and nice private bathroom instead of a cot and shared bathroom. You could say that's being spoiled but the older you get the more likely you have back problems or bathroom problems that the comfort helps with.

[yhoneycomb]

I feel like you're way too defensive about your viewpoint! This seems 100% understandable. This guy is just talking about what's worked from his experience.

If anything, I can't imagine having more money making things harder. Wouldn't you be able to join a travel group? I guess the main issue there is people would probably be coming with their families, though.

There's gotta be some way to meet other bachelors who are decently well off.