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The Second Date Is Her Turn To Ask Me Out

September 12th, 2013 Leave a comment Go to comments

The first date was a car show, because in the city of Detroit, that’s a good date. I learned this quickly, when I moved to the D in the Summer of ’02 to do an internship at the Detroit Free Press. She was a hairstylist, because in the city of Detroit, a good woman does some hair (even if it’s on the side of whatever other career she has) but she just so happened to do it full time.

We met through a coworker of mine who was a friend of hers. I just wrapped up writing a whole package on the car show, which made my date activity choice even more impressive. On our way there, I told her about all the things they had going on at the show. “You did your research on this car show, didn’t you?” she asked. “Well, I wrote about it actually, it’s in today’s Free Press,” I said.

Points, baby. Count those.

In Detroit, everyone is either very into cars or into cars. No one is not into them, at least no one I met, and this girl was no different. She knew her stuff and as much as I wrote about that car show beforehand, as we were walking around, she became the brains of our operation. She could spot 18s, 20s, and 22s without a ruler. I was impressed and for whatever reason, falling for her.

While we sat down to eat some typical festival fare, two gunshots rang out. We got up and ran to the nearest exist, equally fast, and when we got there, slowed down to a speed walk holding each other’s hand. In spite of that brief brush with gunfire, the two of us had a great time. We said our goodbyes, I got a kiss on the cheek, and I went home high on this new girl.

I was 20-years-old at the time, still preoccupied with silly things like not trying too hard, and appearing as though I’m just chilling. This meant I didn’t call her for the rest of the weekend, even though I wanted to talk to her the next morning. Instead, I waited until Monday, after work, to ask her out on date number two.

No sooner did the clock on my computer hit 6:00 did I gave her a call. “Heeeey,” she said. She was happy to hear from me, I could already tell. I, of course, acted only mildly enthusiastic. “What’s up?” I said. After catching up on each other’s weekend, I was ready to deliver the request for a second date, but she stopped me. “So listen,” she said. “I don’t know if you’re free this coming week, but there’s a cookout, and I’d like you to come with me if you can.”

For the second date, she was asking me out. I was shocked. This was unprecedented, and because it was coming from a girl I was actually digging, I think I said “Yes” at the same time she said “can.”

Since I know you’re curious, that date went well. A couple of other dates followed and those went well too. It wasn’t a full Summer romance, more like a June one, and it was fun while it lasted.

The only reason why I’m telling this story is because it was with her I discovered a distinguishing mark of a mature woman: The fearless approach to asking a man out on the second date if the first date went so well.

I initially thought this was something older women did, because she was three years my senior. Her, I-don’t-have-time-for-games-so-let-me-just-ask-you-out-because-we-had-a-good-time-on-the-first-date approach (or whatever you want to call it) was something I thought women did when they were also old enough to drink without a fake ID. But as I got older, I realized age has nothing to do with it, and it’s actually not a rule, even though it kind of should be.

Just last week, I appeared on Huffington Post Live to talk about the complexities of the second date (you can watch my appearance in full at the bottom of this post). As far as dating discussions go, I would say it’s one of the more underrated subjects. Think about all the books and articles written about preparing for and what to do or not to do on the first date. Even at my job at The New York Post, where I set up people on blind dates, the focus is always on that first impression. I’m not out here hooking people up with people they went out with once before. Because the first date, is, well, first, that’s where our focus is, and it honestly should be. Thou shall not get ahead of themselves, is not something written in the Bible but it should be.

Yet and still, anxiety about the second date usually begins the minute we realize the person we’re with on the first date is someone we would like to see again. No matter how good the first date goes, we are left wondering if they feel the same way and when should we ask them out again? Even after the girl in Detroit, I’ve left my fair share of good first dates wondering how I should approach the second one. On the rare occasion a date has gone incredibly well, I have been brave enough to make plans for date number two before the end of date number one.

I have no problem with being the person to ask someone out on a second date, but women shouldn’t have a problem with it either, and yet, I can’t tell you how many lady friends of mine will hit me up after they had a great first date with some guy worried they won’t get asked out again.

Cut that out, ladies.

If you had a good first time with him, be the one to ask him for a second time. If you’re worried about whether or not that obligates you to pay (you did ask, after all), you’re 1) worried about the wrong things 2) not as into him as you think you are because you can’t seem to get over the cost of that second date.

But if you can get over those hangups, then you can get up the nerve to ask the guy out on the second date. Why do I have to ask you out on date number two when it technically took me my whole life to ask you out on date number one?

As I said in the segment, there is nothing more important than a first impression. Absolutely nothing. But once that’s out of the way, don’t be a woman afraid to make a memorable second impression. It’s the second date. There really is no rule book here, but I will happily read one with a rule that says if she had a good first date, she can and should ask him out on the second date.

Check me out below on HuffPost Live

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  • Jeremy

    This was a great read and touched on some great points! I hope you don’t mind, but you hit some great points that really backed up one of my blog posts, so I edited and referenced you in my post. I’m just getting started with my blog and appreciate good reads and inspiration. Thanks again!