Adventures in Dating with a Wingman
Instead of a game you have to play or a trial you have to endure, we believe dating should be an adventure you’re called to embark upon.
However, like any adventure, you can’t expect to succeed without the right crew. And the right crew is always going to include at least one reliable wingman. So to give you a vision for what kind of person you want to fill this role in your life, I’m going to share three fun and unforgettable adventures in dating with a wingman from my own past.
But first, allow me to introduce you to David Edwards, my #1 wingman from my college days, because…
I give a fair amount of credit for the success of my dating life to the guy I double-dated with more often than anyone all my years of dating.
Trust me! When you hear my tales of adventure you’ll want a wingman like Dave too.
That said, some who knew me back in my college days might contest the success of my dating life. After all, I was quite a flirt. Perhaps a tad obnoxious even. Or overanxious. (Read: a lot obnoxious and overanxious)
Indeed, I might have gone out with too many ladies, beginning with over 30 different women my freshman year alone. And yet despite all that effort I couldn’t manage to land a girlfriend until the second semester of my junior year.
However, that girlfriend only stayed my girlfriend for 11 months.
Because I put a ring on it after that.
And 28 years later, she still wears that ring. Just as happily as I still wear the ring she gave me.
I wish that kind of success for your dating life, so lets see what we can learn from these three adventures in dating with a wingman.
OK, so Dave and I didn’t double date to Homecoming, but he did assist me in asking out my date.
He beatboxed (the only Baylor friend I knew who could beatbox) while I rapped my date request at Itza Pizza in the Student Union Building in front of a few friends. And an array of slightly amused on-lookers.
One of those on-lookers happened to be Julie, the girl who would one day become my wife.
But can we be real for a moment? Just asking someone out is a risky endeavor.
Extending a date invitation can feel like you’re giving someone permission to validate your existence. Or invalidate it.
But with a wingman helping me make “the ask,” I already was validated. If the girl said, “No, I don’t want to go out with you,” I could still know Dave had already said “Yes, I will help you ask out this girl.”
All of that to say, my future wife (who didn’t really know me at the time) watched my rapping antics from a distance and wasn’t impressed. However, Dave was so successful in making me look good, the girl I was trying to impress at the time changed her plans so she could attend homecoming with me.
Turns out, she had another guy friend who was already planning to visit her from out of town that same weekend. Guess he didn’t have the mad skills I did. Or maybe he had the right rhymes, but not the right wingman.
Then there was the fun of making a public date invite together. We asked our dates to the freshman formal at the end of a skit in front of the entire Freshman Council (which consisted of about 60+ freshmen).
Thank goodness both young ladies said, “yes.”
Cooler still, the day of the formal upperclassman friends of Dave let us use their apartment to cook and serve dinner. As freshman who had to live in a smelly dorm and eat in a cafeteria every day, hosting two beautiful ladies for dinner in an apartment all on our own felt so grown up.
And that leads to an important point:
Dating should be about growing up.
But sadly today, dating is more often engaged in by middle schoolers who just want to play “grown up,” while high school and college students (and even young adults) opt for hanging out or hooking up. Until their desire for romance or sex (and maybe marriage) drives them to try an ever expanding series of dating apps.
All of that to say, you don’t need a wingman who can beatbox or cook, as much as you need a wingman who will help you grow up.
The Illegal Date
Then there was the date that would become legend, but before I tell you what we did, you first you must understand the following:
- Our dates were a part of a common friend group and already knew us, so there was a level of healthy trust there, and…
- This was before terrorism and dating violence had become as common as it is today.
That said, about 30 mins ahead of picking up our dates, Dave and I both called and told them that (for reasons we couldn’t explain) we wouldn’t be able to come to their dorm. Instead, we needed for them to wait for us at a certain street corner on campus.
Then at the appointed time we sped up to that corner in my Vette (Chevette, that is), screeched to a halt, and jumped out of the car wearing bandanas. We kidnapped our dates at (plastic) knife point and blindfolded them (while they laughed hysterically). Then we picked up our pizza and drove around to disorient them so they wouldn’t know our destination: the Baylor stadium.
It was not a game night, so the stadium was closed. However, at the time the stadium was also under renovation and I had discovered this one obscure place you could easily enter by lifting up and ducking under a temporary fence.
So we got our blindfolded dates out of the car, ushered them under the fence, into the stadium, and down the ramp onto the field. About halfway to the 50 yard line, my date figured out where we were from the feel of the turf and the echo of the stadium. Even still, removing the blindfolds from our dates felt like a cooler surprise than any I had delivered to anyone EVER.
And right there on top of the Baylor BU we had a picnic blanket laid out with all we needed for a great evening:
- Pizza (the food of choice of college students throughout time)
- A cooler with Clearly Canadians (the coolest non-alcoholic beverage known to man in that day)
- A boom-box for ambiance (because back then phones were attached to walls, and we didn’t know what an Ipod was)
- Board games for after-dinner entertainment (because we couldn’t play video games on the phones we didn’t have with us)
We didn’t miss the stadium lights, because it was a cloudless night and the moon was bright.
It was the perfect date!
However, it occurs to me that if Hollywood put this scene in a movie, they would nix the double date part. It would be just one couple. Only two alone on that blanket together, because that’s how things are done in the land of romance.
But, you must believe me, I was as happy to be there with my wingman as I was to be there with my date. And I know our dates felt the same way.
Double-dating kept the focus on getting to know our dates instead of trying to romance them.
It was so. Much. Fun!
Until one of us saw them.
Waco, We Have a Problem
As it turned out, we weren’t the only ones to realize you could break into the Baylor Stadium that night. First we saw just one person. And then another. And then another. Guys running around in the stands, and then hiding. And then jumping up and running to another hiding place.
However, that only weirded us out. Then we heard the first shot, fired from one side of the stands and hitting the other side.
“That was a gun!” one of us exclaimed.
And with that one “pow… ping” my emotions transitioned from jubilation through confusion to terror.
A bunch of armed men, were running around and hiding in the stands, while the four of us sat there completely exposed in the center of a football field that had turned into a field of battle.
I thought it was scary just asking a girl out, but this was another level of fear.
David and I went from playing the role of friendly kidnappers to the role of deputized bodyguards. We quickly gathered up our things and scurried over to the end of the field and up the ramp, where one of the guys sat crouched in hiding, all dressed in black (including black face paint), and holding his gun pointed in the air.
You better believe I was grateful to have a wingman by my side as we endeavored to escourt our dates to safety!
Creative Dating Pro Tip
It wasn’t until we were driving away, and our hearts stopped pounding out of our chests, that Dave suddenly had a thought.
“Turn back around,” he told me. I did, and as we passed the Baylor Stadium again we saw several of his friends driving out of the parking lot, still laughing hysterically at their dating coup d’etat.
The moral of the story is this:
If you come up with a date idea as amazing as a moonlit picnic on the 50 yard-line of your college stadium, wait until afterwards to brag about it.
Otherwise, one of your lonely, loser friends will get a group of guys together to come and bust up your amazing evening.
Well, it actually didn’t bust up the whole evening. We continued the date at Lake Waco where we had already planned to end the evening anyway, with s’mores and worship songs around the campfire.
Although we were there after the park closed.
And that’s why we called it “The Illegal Date.”
I’m not saying you should find a wingman who can help you break the law, but certainly one up for an adventure, and ready to make the best of any unforeseen surprises.
A Wingman is about More than Dating
In the end, Dave and I shared something far greater than great date escapes. We shared a friendship that grew my confidence in both myself and my God. But it did more than that.
Honestly, I could not tell you how much my relationship with Dave meant to me. I came to Baylor only just beginning to break the hold insecurity had held on my heart all through middle school and most of high school.
I needed a friend like Dave. He was supportive, fun, creative, and faithful! He was a GREAT friend to me, back when I was only beginning to learn how to be a good friend to anybody.
But can you guess who is just as grateful today as I am for my friendship with my #1 wingman from college?
That would be my wife.
Julie might not have been impressed with Dave’s beatboxing skills back in the day, but Dave helped teach me how to be a good friend. And…
In learning to be a good friend, I was preparing to be a good husband.
In learning to share the ups and downs of dating with Dave (and many other fabulous guy friends I cherish from Baylor) I was preparing to walk out the “for better or for worse” covenant of marriage.
So, if you’re a man of God looking for your future wife, you want to find a dependable wingman first! And if you’re a woman of God looking for your future husband, you want to look for a man who walks with other men of God, because no one should embark upon the adventure of dating alone.
And neither should you.
Want more guidance in how to succeed in dating? We have a Hot Topic resource page to help!
Our LoveEd discipleship series, Beyond Sex & Salvation, will empower you to grow spiritually and date wisely, so you can marry well.
This discipleship series is NOT for couples, but for the wise individual who wants to prepare for their future marriage like a successful career: intentionally, intelligently and IN ADVANCE!
This discipleship series is NOT about dos and don’ts. It’s about learning the life lessons, mastering the life disciplines, and making the life decisions necessary for relational success.
Check out all three study guides. You can walk through them on your own, but it’s more fun with friends (that and it kinda makes sense to grow in relational success in actual relationships with others), so consider putting together an FMU LoveEd small group study.
Even better? And ask a rock star married couple you respect to lead it!