OK Super, before posting my thougts on the dating process, I want to clarify what I meant regarding the pursuit of a careear.
No one would sugesst that a 15 year old be expected to earn their room and board by working part time. The job of a 15 year old to be a student.
But once you are ready to run a household of youy own, you should be prepared to meet the expenses a family will entail. It may be several years before you have to start paying tution, but its very much on the horizion, and for a bocher to enter the family market without being able to meet is responsibilites is irresponsible. Which is not to say that the job overrides torah values. On the contrary, meeting your financial obligations is very much a torah concept. That said, here’s what I can share with you about the next phase of your search:
Much of what has already been posted is the fundamentals, so let me just repeat a thought from Rav Pam ztl:
When asked, “what should I look for in a spouse?” he replied, “thats like asking me what bus should I take.. if I know your destination, I can advise you which bus will get you where you want to go.”
What to look for in a shidduch is largly dependent on the goals you set for yourself in life. If your dream is to have a house that is always open to guests, and routinly bring home 2-3 people right from shul, its a good idea to be sure you discuss this ahead of time so neither of you are disapointed.
If you expect to have a television-free house, it would wise to mention this as well. And don’t count on the shadchan for having cleared all these hurdles. Your idea of a “chesed filled house” may not be the same as what was relayed in the information gathering / sharing process.
And for what its worth, I started the dating process right after sukkos, and was engaged during Channukah, so hopefully, your search will be as smooth.
Also, if you’ll be dating in the NYC ares, I have a great lead for you; Roosevelt Island. Its an easy drive, there is a parking lot as soon as you enter the island, (and is subway accessable, if you prefer that) and is way less crowded than the standard dating venues.
While the 1st, 2nd and even 3rd date should be by car (your own or rented) its a good idea to see how she reacts to a minor setback. Not what you want to try on every occasion, but a small test to see if she is really committed to making things work, even when its somewhat of a hassle. Life is going to throw you an occasional curve ball, see how good your teammate plays under pressure.