I'm by no means the authority on dating rules, but here's a short compilation of my own reflections regarding "in-date" moves in this dating game.
🙅🏻 Don't mention the future (between you and your date) when you've only just met the person and have no idea where it's going.
While I was on a date with a fellow, he made a reference to his mother's Pesach cookies. "They're so good, you really can't tell they're not chometz," he said, "You'll see."
Um, will I? It was a second date, in January.
🙅🏻 On the flipside, you don't need to keep prefacing statements with "If we're still dating..." when talking about the future with someone you've been dating for a bit. It's obvious that these things will only take place if you're still dating, and they won't if you're not.
I was dating someone for awhile, and he kept making references to all the things he wanted to do together "if we were still dating." It was almost as if saying I exist in his future was a commitment of sorts he wasn't ready to make.
🙆🏻 If you're in the position that you're responsible for planning the date, have something in mind to do. You don't need to have it planned out from start to finish, nor do you need twenty different options, but please, pretend that you gave it some thought. It means that you respect the other person and this process.
Reference Mr. I'm-Going-Snowboarding in the sixth paragraph of this post.
🙅🏻 Don't always take your date to a hotel. It's this weird thing we do, haunt hotel lounges. Is it because we need a public place to hang out? Are we too cheap to go to places that cost money? Are we just not creative enough to figure out where to go on a date?
Back in the early days, I went out with a guy twelve times. Ten of those dates were to hotel lounges/lobbies. It was great in the sense that we got to know that we could entertain each other with just our intellect/conversation, but beyond that it was incredibly flawed.
Nowadays even one beginning hotel date is too much for me. If you need ideas, I'm happy to provide.
🙆🏻 Run date plans by your date. Especially if you're on her/his turf, there may be places that s/he's not comfortable going for whatever reason. It may be as simple as your pick of locale is somewhere where s/he may run into many people she would rather not while she's on a date, or perhaps there are other reasons depending on what the venue is.
One Friday afternoon a guy picked me up for a date. He thought he would take me somewhere nearby, because after all it was Friday and we didn't have a lot of time. His pick of location happened to have been somewhere where the entire frum community hangs out on Fridays. Normally I don't care about who I see while I'm on a date, but there are certain places you go with your date if want to make a statement that you're serious about this guy, so you don't care who sees you with him.
🙆🏻 If you're eating or drinking something on a date, offer your date, the same thing you would do with a friend. It's impolite to get a drink for yourself but ignore the fact that you're with someone. Rookie mistake. Always think about the other person you're with.
There are too many examples of people not thinking about me, so I'll give you an example of someone who did it right.
Seems like he stopped for a drink while filling up gas on his way to pick me up. He had gotten himself a drink, so he got one for me too and offered it to me when I got into his car.
Another time, I had traveled to meet a guy for a date, and before I left to go home, he walked me to my car and gave me a care package for the ride back. It was a little awkward because he also asked me to let him know when I got home, and I wasn't even sure if I wanted to go out with him again. But even so, it was really sweet.
🙅🏻 Be genuine, but match your transparency level to date number, how well you know your date and mutual comfort level in the relationship. Dating is much like real life. It's not socially appropriate or emotionally fair to spill your guts or air dirty laundry to someone you've only just said hello to. Once you've even just established a baseline, this changes accordingly. Pay attention to social cues.
Case in point, warning from the guy about his crush in the second to last paragraph here.
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