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Oct 12

How to come up with date ideas

Sometimes it’s hard to know the right answer

They say that relationships formed in stressful situations never last.

To them I say, “No sir! No!”

Well ok they might be right, whoever they are, but a decent relationship built on a shared stressful situation beats no relationship, or a straight up bad one, any day. I won’t lie, I have planned dates that would put both of us in a challenging or stressful situation just to sort of help along the bonding.

That having been said, let’s talk about dates and what goes into figuring out what would make a good one, and what makes a bad one. You’ve heard of my Scandinavian Toilet Paper Holder Shopping date, so clearly I have some experience with the latter but what of the former?

When setting up dates it’s important to ask yourself some key questions:

  • What things do I enjoy doing?
  • What things do they enjoy doing?
  • Is this the first date? Third? Fifth or beyond? (arbitrary numbers … basically which date is this?)
  • Do you want to stay in your comfort zone or do you want to expand your horizons?
  • If this is a first date, will there be ample opportunity for conversation?
  • If this isn’t a first date, do you still feel you need to use this opportunity to get to know them?
  • Can you afford it?

And so on and so forth. Everyone is different, both in the position of trying to plan a date, and in the relationship/interaction you have with someone. In Sports Night the advice is given to Pick a place that you like. That’s valid advice I think as you’ll probably feel more comfortable and confident in familiar surroundings, but I think there’s just as much evidence behind picking someplace They like as well.

I make no claims to be an expert at dating by any stretch of the imagination, but generally I try to pay attention (without actively trying to try) when first talking to someone and base my date decisions on what I learn. One girl was a friend of my roommate and, over dinner one evening when I first met her, talked about how what she really wanted was a laser scope for her revolver. So since we’d sort of talked a little bit, I figured it might set her at ease to do something she presumably enjoyed and I took her to a shooting range on our first date. The full extent of my handgun knowledge at the time included knowing which end to hold, but that’s about it. I figured it would put her in a place she’s familiar with and probably enjoys, allow her to feel confident and teach me something, and then we could go get dinner afterwards. Unfortunately she was really insecure and didn’t want to shoot at all, so that didn’t go entirely as planned but it gave us something to laugh about.

Another girl talked about how she liked hiking, so I suggested that we meet for the first time at a local park where we could do some hiking. As we got closer to the day the weather turned sour and rain was in the forecast. We both acknowledged that it might rain and decided to go with it anyway figuring that we could work something out when we got there. I met this girl on the internet, so the first meeting was a little different (at least it is for me). We showed up, it was raining, and we decided to just go for our hike anyway and to just deal with it. That was one of my favorite first dates ever. Hiking in the rain is AWESOME! Conversation with this girl was equally fantastic, and we really hit it off.

I’ve had picnics at a park in the city, coffee at a random and unknown coffee shop for safety’s sake, I’ve played massive outdoor chess, visited modern art museums, science museums, and shared countless meals. After all that my takeaway is that what works is largely dependent on whether there’s chemistry. If there’s chemistry you can take me shopping for toilet paper and cosmetics and I won’t care. I’m not most men … but still.

Second and beyond dates are even more dependent on what works for the two of you specifically. If you’re married this is more challenging but also more exciting. You already know each other so you can focus on trying new things, surprising each other by remembering things that were said in past weeks, months or years. The key is listening. People say things when they don’t even know they’re saying them and it’s on you to pick those little clues up. That’s the difference between a nice night out at an Italian restaurant and a hike in the rain or an appropriately timed and written poem. Sometimes you just need to stop and listen.

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