My Fifty First Dates

first-date-young-manWhen I look back at my youth, I sometimes cringe about all those first dates and how awkward I was. A lot of men worry about making a bad first impression, fearing they might do something stupid like forget to bring their wallet or accidentally show their date pictures of their wife and kids. Bad form.

I’ve been out of the dating scene for a few decades, but I doubt it’s changed much. The last time I asked out a woman other than my wife, Margaret Thatcher was the newly elected prime minister of Great Britain, Christopher Cross had just topped the music charts with Sailing, and a surefire way to pick up chicks was to impress them by riding the bar’s mechanical bull. Um, okay, maybe things have changed a bit since I was making my moves.

I’ve had lots of experience with first dates – and even a few isolated experiences with second dates. I won’t sit here and brag that I’m God’s gift to women – and I’m pretty confident neither would any of my first dates. But I can vividly recall how some of those entrées into the dating world went. I’d like to share my wisdom around this important mating ritual, in the hopes it may help some of you single guys out there have a better chance at a second date. (I swear I’m not making up any of the following examples).

If you’re in say, middle school, and you’re on the very first date of your life, don’t put your arm around the girl during the movie unless you pick up clear signals she’s into you. Subtle signs she may not be into you include:

  • She stares at the screen the entire time, refusing to make eye contact with you
  • After five minutes, she discreetly removes your arm from her shoulder – and does it again five minutes later
  • When your older brother picks you up after the movie, she asks you to sit in the front seat instead of the back seat with her
  • When you attempt to walk her to her door (as your father told you was the gentlemanly thing to do), she sprints

These all happened to me on my very first date. I felt so crushed that I briefly considered the merits of changing my sexual orientation.

first-date-bullPerhaps no date is more important than your senior prom. If you were like me, by your senior year, you were just glad to finally have your braces off. And your prom presented the added anxiety of being a first (and last) date with the prettiest girl in your church.

Here’s a suggestion: When you return back to her house after the formal prom, to prepare for the after-parties, you might want to make sure your car is actually in driving condition. While the following scenario is admittedly unlikely, it’s possible your car may break down in your date’s driveway at 11:45 pm, and as you attempt to put the car into reverse, it just might cause the horn to blare incessantly, waking up her parents. And you may just have to abandon your car – and your date – and walk home in the pouring rain – in your soaked formal attire – I’m just saying, it could happen.

A first date you might want to avoid is one with someone who’s already engaged to someone else. Take this example – which is totally hypothetical (other than for the fact it happened to me in my freshman year of college). Say your college dorm mates enter your name into a campus computer dating event, matching you with complete stranger for the big dance – without telling you. And say you decide to move forward with this date – because you know it’s the only date you’ll get that semester.

When you meet your computer-matched date, you might want to ask her, “Hey, just curious. Are you currently dating anyone?” And failing to make that inquiry, when you decide to proceed, and then her fiancé walks in on the middle of your date, at which point she confesses she’s engaged and asks you, “Do you want to see World War Three begin or do you want this date to be over with now?” (that was an exact quote), you might want to resist your knee-jerk urge to make a bad situation worse by flippantly responding, “Actually, if you don’t mind, I’d like to go with the first option.” Trust me, that’s not the correct answer.

When you ask a girl out on a first date in October, and she tells you that she’s super busy this weekend, and then you suggest the following weekend instead, to which she replies with (and I’m not kidding), “Actually, I’m going to be pretty busy through April”, once again, resist your smart ass instincts to say, “That’s cool. So what’s your May look like?” It doesn’t improve your chances, I learned.

first-date-couple-in-restaurantFinally, when you ask a woman out on a first date to see a football game, you might want to find out beforehand whether she actually likes football. In my case, it turned out my date hated all sporting events, but apparently not enough to turn down my offer of a date.

So let’s just say you’re lucky enough to have her say yes for that football game. Then you might want to avoid choosing a night game, in a high-crime section of Miami, in an area where almost no one speaks English. And then, after the game is over, you might not want to completely space on where you parked the car. In the highly unlikely event it takes you TWO HOURS to finally locate your vehicle, and your date opted to wear 4” high heels that evening as the two of you roam from car to car like refugees trying to locate their tent in a sea of 10,000 tents, you might want to start thinking up an apology speech as emotionally stirring as the Gettysburg Address. Because that’s what it’s going to take for her to EVER want to see your face again.

Apparently my apology speech hit the mark. Because 29 years later, that woman in the 4” heels is still my wife.

That’s the view from the bleachers. Perhaps I’m off base.

Tim Jones - Profile at Safeco - TinyPS: If you enjoyed this week’s post, let me know by posting a comment, giving it a Like or sharing this post on Facebook.

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  • Published On Dec. 04, 2016 by TEJ
  • 3 Comments


    1. 12/9/16

      Finally, a column with great advice. Here’s a story that fits. I took a date to Seattle to attend a Mariner’s game when they played in the Kingdome. She didn’t want to go because she was concerned about walking through what appeared to be a crime-oriented area to get to the game. We did go, and it turned out to be “bat” night. The first 5,000 fans to enter the stadium received a Mariner’s bat. After the game we all walked out through that same “crime-ridden” area. The Seattle police reported in the P-I the next day, that they had the lowest crime rate ever in that area. My date said, maybe we should carry bats with us all the time. Needless to say, we got married.


    2. 12/9/16

      The young man in the photo, although he forgot the day of the week to meet whomever, he looks sincere and he’s really trying to be cool. Give the poor-sod a second chance.


    3. 12/12/16

      I love a story with a happy ending.

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