How to Be a Dating “Wingman”

friends
Helping your friends date in community is much more than tagging along as a third wheel.

“I’m thinking about saying yes.”

Was she –?

Yes! My normally romance-resistant friend Justine was blushing just thinking about dating Jordan, our mutual friend.

The next couple of months felt like something out of a Jane Austen novel as one or the other – or both Jordan and Justine – would stop by my home and talk, usually while drinking a large mug of tea. Sometimes I was a sounding board; other times I simply provided a safe space for them to get to know one another better.

It was time-consuming, rewarding, hilarious – and sometimes messy. I had a lot to learn about supporting my friends as they date.

Defining the role

Sure, I could call myself the “third wheel.” The term describes a single friend who accompanies a dating couple – but it can also mean unwanted, useless and unnecessary. Seriously? Instead, I’m going to use the term “wingman.” While it’s not always a positive role in the context of dating, in an Air Force context, it’s vital: When you’re flying first in formation, the wingman guards your tail.

Dating in community helps couples stay accountable for appropriate physical and emotional boundaries, maintain important friendships, and avoid becoming codependent. The presence of others also helps identify relational red flags and gives greater objectivity in issues of character and compatibility from multiple angles and stages of life (Proverbs 18:1; 11:14).

The wingman’s many faces

Supporting a dating couple becomes a lot more doable when you realize that you’re only part of a larger team (Romans 12:3-6) and that each wingman role may be as different as the friends involved. One (or more) of these roles may describe you, while the rest will (hopefully) be filled by others in the couple’s circle:

  • Comrade-in-arms: Because you’re in the same life-stage as the dater, you can easily swap insights while telling your own stories. Sometimes you interpret his experiences to others so they can support him better.
  • Encourager: You help the dater regain perspective when she misreads or overreacts. You may provide an actual shoulder to cry on, shed tears on your friend’s behalf, or simply listen and express compassion. You may pray for her on the spot or promise to continue praying until things change. You also bring her attention back to Jesus and His good purposes, and hold onto hope for her future at times when she’s discouraged.
  • Problem-solver: Perhaps you are well-read, have the gift of discernment, can draw from the experience of mentoring numerous friends, or are trained as a counselor. You recognize patterns in the way your friend dates, help troubleshoot underlying issues, and recommend books and resources.
  • Mentor: You have maturity and life wisdom that the dater needs. Though you may be unable to fully empathize because your story is different, it means a lot when you make a genuine effort to understand.
  • Accountability partner: You support your friend in maintaining the boundaries he has chosen and communicated with you.
  • Connector: You foster interconnectedness in dating by inviting the couple to help clean up after a meal, pitch in during a move, or serve together at church; to join you for meals, Bible studies, small groups, parties, game nights, double dates or informal couple-to-couple counseling.
  • Sounding board: While your friend figures out healthy expectations, progression and dynamics for the relationship, you’re an active, sympathetic listener. You listen to the end, summarize and ask if you’ve heard correctly, support while gently suggesting other possible interpretations, speaking from Scripture. You’re willing to let your friend process the same thing repeatedly.

Remember, a good wingman has good boundaries. Respect both partners, refusing to give into gossip or “piling on.” Keep your discussion confidential except in cases of abuse, and avoid imposing your personal relationship ideals or applying your experiences to those in a different situation.

Encourage your friend to vet your advice, and make sure they know communication will stay open even if they don’t take it. Finally, pray more than you advise or attempt to “fix.” God knows your friend’s situation better than you do, and is eager to provide guidance when asked (James 1:5).

Offering your services

I met Kailyn in an online forum. Because we were both dating at the time, it was natural for us to share stories as we became friends. Soon we were zipping video messages back and forth, asking, “Am I crazy? Do I have a right to be stressed out about this?” Then we’d encourage one another, as Kailyn says, “to respond biblically and not get trapped in the feels.”

In many cases, the wingman role arises naturally out of an existing friend, sibling or mentoring relationship. Ideally, your dating friend will simply invite you to be a wingman, and you won’t have to wonder what your role is. But how do you support someone who is not bringing up the latest in her dating life or asking for prayer and advice?

First, understand that not every friend needs you as wingman. Though I felt uneasy when an acquaintance began dating a man with a complicated past, I knew that because she already had wise, highly involved family and friends, it wasn’t necessary that I jump in to help her.

If you are a key person in your friend’s life and she’s not sharing with you, then it might be healthy to ask yourself: What kind of person do I turn to when I need help with dating? I’m guessing you choose someone who feels safe because she is committed, not to a specific outcome, but to God and your true well-being; because she shows you respect, is open about her own life and shortcomings, and views you not as a project, but as a friend.

If you’ve determined that you are easily recognizable as a safe confidante, then perhaps you can simply bring up the topic with your friend and establish the details of your role together.

In his book “Side by Side,” biblical counselor Edward Welch gives us what he calls “a primer on how to help one another.” Step by step, he describes what it means to initiate and deepen a mutually helpful friendship with a fellow believer.

First, whenever you cross paths with this person, greet her. Sound ridiculously simple? It can be life-changing. Gradually, in short but meaningful conversations that grow longer and deeper, you’ll begin discovering what’s important to your new friend. As you swap stories and life updates, it becomes natural to pray with and for each other. When sin arises, you’ll be positioned to act patiently and humbly, and because all this plays out in the context of the body of Christ, you’ll enlist co-helpers when needed.

When wingman work gets messy

Fighting panic about a long-distance relationship that was reopening old wounds, I called my parents for comfort. Normally they’re the best of wingmen, but this time I heard a new message behind their words: This is your fault. Forget others’ happy endings; get used to your story being hard in every way.

Bewildered and hurt, I hung up the phone. “Why would anyone say that?!” I exclaimed. That’s when I realized: Because I was teetering on the edge of panic, my emotions had distorted what they actually said to me.

Has dating blindsided you by revealing character flaws you didn’t know you had? It could be heightened sensitivity, insecurity, jealousy or unrealistic expectations. Perhaps it was fear: of rejection, making poor decisions, or bystanders thinking badly of you. For some, it’s easily crossing physical boundaries because you’re too trusting of your normally excellent self-control.

If you can relate, then you are even better prepared to express compassion to your dating friend who’s been blindsided as well. You can voice Jesus’ love and reaffirm your friend’s identity in Him. You may also share your own dating stories so your friend knows when his concerns are normal and when they’re deal-breakers. If your friend’s response is unusually strong, you may encourage him to look beyond symptoms for root issues like learned behaviors, relational scars or dysfunctional family patterns.[i]

If there are true red flags in your friend’s relationship – his partner is manipulative, abusive or involved in unaddressed addiction or sexual sin; or maybe the couple is together violating the Bible or their own stated boundaries – then how do you address them?

Edward Welch suggests that you pose the scenario anonymously to your pastor for advice. Or wait until you can talk privately to your friend without interruption and ask if he has noticed a specific behavior, and if so, how he feels about it. Be direct and compassionate, saying, “Hey, I’m concerned about ______ because I love you and don’t want you to get hurt.”

Why wingman work is worth it

At times, the wingman role is especially difficult. You can feel tired, lonely, or left out. When someone is getting what you’ve waited for, it’s tempting to pull away. It’s never fun to provide accountability – and in addressing such sensitive matters, you are taking a real risk that your friend will become hurt or angry or even reject you.

But I learned that ultimately it’s not about me, my friends, or getting someone to marriage, because both dating and serving as a wingman have been excellent means of growth. My friends and I have become more realistic about how relationships work, and less likely to over-think or fear them. We’ve grown in humility and reliance on God, our understanding of temptation, compassion for ourselves and others, and hope as we discover that God truly is the best matchmaker.

There’s also much to enjoy in the process, including the excitement of hearing about the unfolding relationship and the way it can bond you as friends, getting to know the new boyfriend or girlfriend, and celebrating growth and hard decisions made wisely. Because I share a personality type with some of my friends’ husbands, a simple conversation about my motivations can provide them parallel insight into their spouses. Even as my role in their lives shrinks or changes, my married friends continue to value my friendship and need my support. As my friend Joy reminded me, “You’re a necessary part of the process, not just a third wheel.”

Perfectly positioned

“Hey, Allie, look at this!”

While I was at work with a girl I knew my younger brother was secretly interested in, he just happened to text me a picture of his building project. Sharing the photo was a fun but rare moment, because as her older mentor I knew she valued my opinion, and I wanted to leave Allie space to form her own feelings about Dan.

Months later, I delightedly helped break the ice after their second date by serving them hot chocolate at my kitchen table.

Finally, I wore a flowing blue bridesmaid’s skirt and walked a grassy aisle to stand opposite my teary-eyed brother while he married one of my dearest friends. Having closely witnessed their sorrows and uncertainties and God’s many providences as He brought them together, their joy was my joy, too.

Sometimes the third wheel has the best seat in the house.

***

[i] Three books that helped me understand my own insecurities and form healthy patterns in dating or wingman relationships were “When People Are Big and God Is Small: Overcoming Peer Pressure, Codependency, and the Fear of Man by Edward T. Welch, “The Sacred Search: What If It’s Not About Who You Marry, But Why? by Gary Thomas, and “Love Across Latitudes: A Workbook on Cross-cultural Marriage” by Janet Fraser Smith. I found the last book helpful for other unusually complex relationships as well as cross-cultural ones.

Copyright 2021 Elisabeth Adams. All rights reserved.

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About the Author

Elisabeth Adams

Elisabeth Adams has lived in five states, one Canadian province, and the captivating city of Jerusalem, where she studied historical geography and Hebrew. As a freelance writer and editor, she loves hearing and telling new tales of God’s faithfulness. Most of all, she wants to keep a quiet heart.

 

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