Let’s face it, sometimes one date isn’t enough. If you really want to increases your chances in this dating game, you’ve got to maximize your opportunities.

Five Dates in One Night

Let’s face it, sometimes one date isn’t enough. If you really want to increases your chances in this dating game, you’ve got to maximize your opportunities.

Let’s face it, sometimes one date isn’t enough. If you really want to increases your chances in this dating game, you’ve got to maximize your opportunities.
Nataliia Vzhyshnevska / 123RF Photo

Yup, I recently had five dates in one night, and you should consider doing the same thing. Hold on. This isn’t some crazy Tinder, swipe-fest story. Those are better left to my fictional alter-ego, The IntimiDATER. This is really a story about my philosophy of a great way to spend time with ONE person that you’re interested in. I’ve previously referred to the perfect date as a “walk” and this is really the same thing.

I met up with her and she was great and we had good banter, but then happy-hour was over. I don’t know about you, but I hate paying full price at the same place that I had been paying happy hour prices. Since we were having a great time, I decided to ask her out on a second date, right then and there. “Would you like to go out to dinner with me,” I asked. Spoiler alert … she agreed.

The change of venue has some great effects. You are now sharing multiple experiences instead of just one experience. You also get to go somewhere together instead of just meeting up. This is a seemingly subtle distinction, but it seems to mean something like that you are together and not strangers.

I also enjoy the walking between these impromptu dates. You are not distracted by servers and food and drinks and whatever else the ambiance is broadcasting. It’s just you two. Do you still have things to talk about? Do you end up holding hands? Do you get to protect her from a would-be purse thief? The latter would be an amazing opportunity to show your inner-superhero. Alas, I was not afforded that chance. I’d have to rely on some Midwest charm and JD wit. I think it worked, but I always think that!

I won’t go into the specifics of each “date,” but I will say that between the restaurants and bars we popped into Bed, Bath & Beyond. That was a fun! There are so many conversation starters in there and walking through, added a new dimension to the evening. I think it’s “our place” now.

After that, we circled back to the original date and ended where we started. Poetic. We now have a joint that we’ve been to more than once. We seemed comfortable there and with each other. I mean, it’s a significant improvement over the tired “coffee date” that always seems more like a rushed interview. (My views of coffee are well documented.)

What do you think of squeezing five dates into one night? If you are in Los Angeles, there are places built to make this happen. The 3rd Street Promenade is the easy choice. There’s also Old Town Pasadena, Downtown Burbank, West Hollywood, etc. If you really know what you’re doing or get some tips ahead of time, you can explore an area of downtown Los Angeles, too.

I felt great about it. I highly recommend the five dates in one-night, plan. I’m hoping dates 6-10 come up, soon!

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Jeff Daly
Jeff Daly is a single (straight) man living in West Hollywood. He is the Chief Awesome Officer at DalyDose, a SAG-AFTRA actor, a photographer and an avid spin class teacher. He is originally from Kalamazoo Michigan and studied economics at Kalamazoo College. He served in the Marine Corps, enjoys fine beer, good food and good friends.

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