If you happen to be in the big cities like New York, London, Bangkok, Los Angeles and the like, then there are both expat and local men who get out everyday, either for the breakfast, lunch or dinner. Finding a way to talk always depends on you. Ask for salt or pepper, enquire about the coffee, see if he is a local or a foreigner from another country and so on. At times, if you can stand right behind in the line while ordering something, then having a small talk in one way or the other is possible. Rich men like to eat outside a lot. Some may cook once in a while, but if they are single, then it is always preferable to have a meal outside rather than cook yourself or hire a chef. Going for a meal outside helps to keep active, gives some exercise and helps to socialize as well. If you do get to talking with a older man, make sure to ask about the work, if they are single and set up a date in the near future, may be the next day itself.

The thing about having money is that you have the time to get fit and rich men like to do that in plenty. Find the gyms in the rich neighbourhoods and start with free trials preferably. Some of the gyms may have a younger crowd, then move to the next one. At times the timing may not match, the older men may frequent the particular gym in the evening rather than early morning. Now, once you have found the right gym, then comes the harder part. How to make the move so that you get to talking to each other. Finding the right situation is the trick. If he happens to do some tough exercise like lifting weights, then helping out is a possibility. If you are carrying some energy drink, then offering an extra bottle is a possibility, especially when exiting from the gym, that is the time when you both are relaxed and are ready to mingle a little. 

Many rich men like to have a drink and at times have their favorite hangout pubs as well. Some of them may be new in the city, on a business trip, visiting the city either for pleasure or for work, and accordingly may sit alone on a table to have a drink. Going with another friend in the beginning can be an option if you are not comfortable, going to a pub alone. Mind you, it is possible to have a soft drink or a mocktail as well in a pub and there is no compulsion to have a drink although it is very much a possibility if you so desire or like to have a sip. Finding an opportunity to have a talk is the next step. If you are with another friend or a group, then asking a single older guy to have a drink with you is always possible. Move towards have a conversation, know about their work and relationship status. If things are as per your liking then deciding to ask him out for a date is the logical next step. Make it sound casual and then meeting the guy alone for a date is the next step. The door to a relationship with a rich old man is now wide open for you. 

Due to the level of privacy that dating apps provide in terms of not having to scout for a date out in the open, rich men in various professions use dating websites these days. Rich men like to have the choice in their hands and the dating platforms give them the option to browse women in any of the famous cities they are in. Women can drop in a profile as well and mention what they are looking for. For example, on MeetOutside there is the option to mention Preference Category that is the profession or lifestyle of a partner that you are looking for. There are matches based on this or women can use AI based text search for filter the older men in rich categories like Finance, IT, Technology and so on. It is such an amalgamation of technology with the human desire, that gives opportunity to women to meet rich guys as per desire on dating apps.