Informalities

Is there something to be said for informal dates? Does every date need to have a tachlis? Can you get to know someone better if you just hang out and chill without necessarily having an agenda? Is this appropriate and/or helpful?

There are so many different opinions regarding the answers to these questions. Obviously a large part of that would have to do with the community one identifies with. The more in-the-box yeshivish one is, the closer s/he is to that side of the spectrum, the more focused his/her dating will be probably. But there is a different aspect here, too, to consider.

How well can you really know someone from going out a few times (even if "a few" is 20 over the span of two and change months)? Are we dating to "know" someone, or are we dating to make sure basics are there and if there is that potential we're seeking?

Personally, I like informal dates. I don't think there needs to be pressure to "accomplish" something each date. However, I do think that each date should build on each other. A fourth date should not feel like a first date. By date four or five the two people should be beyond small talk and even able to have a conversation about where they see things going. Although, there are no hard and fast rules, and everyone at their own pace (as long as the two people are on the same page with that).

Informal dates are helpful to observe someone in a more natural habitat. Shidduch dating can get very artificial. It's fairly easy to show your best self if all you have to do is sit in a hotel lounge or restaurant for a few hours. Less so if you spend many more hours with someone not necessarily feeding them canned lines about your goals and aspirations that were made up to impress them.

I think it's important though to not get carried away and turn shidduch dating into a very informal girlfriend/boyfriend relationship with lots of texting and late night phone conversations. That stuff might start from a real place but often gets inflated. It's also not helpful when you're trying to work towards marriage; it can lead to things getting cloudy.

I'm all for chilling and getting to know someone slowly, but just be aware that there actually may be some hidden mines in that terrain that you may have to navigate.