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Want to Help Your Friends Find Love? Be Their Wingman

If love is a game, then I like to be the cheerleader

“Alison, you don’t have to if you don’t want to. I know it’s a lot to ask,” my friend spoke nervously into the phone.
“Don’t worry,” I responded. “I’ll be there.”

I still chuckle when I think back to that conversation — the time I once agreed to station out at a restaurant for a few hours while my friend went on a first date nearby. It was her first time putting herself out there in a while, and from the sound of her jittery voice during our call, I could tell she’d appreciate some moral support.

Now, I don’t usually go to such extreme lengths — especially when it comes to others’ romantic lives. I trust my friends to date self-sufficiently and know that they are fully capable of going through the motions on their own.
Still, while this happened to be an extenuating circumstance, I can relate to the uncertainty that comes from putting yourself out there in the dating world. As a girl who never had an older sister growing up, I often wished I had a guiding figure to offer me sound relationship advice when I was younger.

So instead, I like to do whatever I can now to help others feel confident and empowered as they chart their own paths. No matter the age, it’s nice to have someone cheering in your corner and encouraging you to be true to who you are — regardless of how the dates actually go.
That’s why, over the years, I’ve gradually taken on the role of self-proclaimed “hype person.” Am I necessarily an expert when it comes to this stuff? Not more than anyone else. Do I still like to root for others and let them know their worth? Absolutely. After all, just because you’re single doesn’t mean that your journey has to be a solo one.
How can you be a supportive hype person for the people in your life looking for someone special? Here are five things I like to do.
1. Help calm their nerves before a date.

One of my friends is a big Taylor Swift fan. She knows every song like the back of her hand and can spend hours educating me on T-Swift’s discography — from the early Fearless days to her more recent albums, like Folklore and Evermore.
On the occasion that I’d come over to help her get ready before a date, she’d often have Taylor Swift music playing from speakers in her apartment. She’d work on her hair and makeup as we both danced around singing “Love Story” on repeat. In the moment, I’d playfully mock her for her Swiftie obsession, but looking back, I can’t help but admire her for her pre-date ritual.

Even though it was simply jamming along to feel-good music, her love for her favorite artist brightened her mood and kept her in the present moment. It reminded me how important it is to have a little boost to feel calm and collected before a date — and that doesn’t necessarily even require music. It could be wearing a certain outfit that makes you feel fierce, giving yourself a motivational pep-talk in the mirror, or eating a healthy snack beforehand, so you have some food in your stomach before you go out.
Before a first date, it’s easy to get in your head or dwell on factors outside of your control. You might begin to overthink about what to say, how to act, and what will happen in the future. You may feel unnatural and out of character. But doing a familiar activity that showcases your personality will remind you to just be yourself and have fun with the process.
After all, who doesn’t love an excuse to get dressed up, go out, and spend some time getting to know someone new? Regardless of the outcome, preparing for a date can be just as enjoyable as the date, itself.

2. Check in and emphasize safety.
When I first moved to New York City, I lived with a suitemate who quickly became like a big brother to me. He was caring, protective, and demonstrated that he had my best interests at heart when it came to my safety.
Before I would go out and meet someone new, he would ask me the location I was going to and the person I would be meeting up with. He made sure I knew how I was getting there and also made me promise to let him know if I ever felt uncomfortable or needed an excuse to leave.
Even though his gesture was simple, it always made me feel safe and comfortable knowing that someone was looking out for me, and I was grateful for the emotional support. While not everyone may feel comfortable disclosing every detail of their dating life to others, it helps to have at least one person you trust who you can share your plans and whereabouts with — especially when it comes to safety.

This can be sharing locations with each other, sending a quick “check-in” text, or waiting up for them to get home, just to ensure they’ve made it back safely. Regardless, both you and your friend can have peace of mind knowing everything is going well — or you’ll be able to swoop in and save the day if not.
3. Encourage them to communicate openly.
This is a skill I’m still working on, especially as a people-pleaser — but since becoming a writer, I’ve learned the value of open communication and choosing my words with care. Not only is this important in the writing world, but it’s an equally valuable skill to have when it comes to relationships.
Especially when two people are first getting to know each other, it makes all the difference to be open about where your minds are at and how you’re feeling throughout the process — especially in the early stages.
If someone is going to be a part of your life, you want to know that you can speak freely — about the light-hearted stuff, but also when it comes to the weightier conversations, like goals, values, and what you’re both looking for in a relationship.
For example, I recently had a close friend in a common modern-dating predicament. She had been on multiple dates with someone she was excited about the possibility of moving forward with, when one day, she could sense him becoming more distant and taking longer to respond to her messages.
“What should I say to him?” she texted me in distress. Many of us have known the feeling all too well. I could tell she was nervous to rock the boat out of fear that she’d push him away. But she was also afraid of staying in limbo, where she didn’t know where she stood. If he was losing interest, she wanted to have clarity.

So, after careful consideration, I encouraged to reach out to acknowledge how she was feeling and ask him respectfully where his mind was at. At first, she felt uneasy. “Is that being too forward?” she asked. “Maybe, I should just wait it out.”
I reassured her that communicating your feelings is never being pushy or asking too much. It’s simply being candid, sharing your boundaries, and establishing the precedent for open communication in the future. Everyone is worthy of healthy and fulfilling love, and if his answer wasn’t what she was looking for, then she deserved someone who could invest in her equally.
As it turned out, the response was a positive one — the guy she was seeing called her soon after to apologize and explain the reason for his lack of communication. Not only did he do that, but he asked if he could start seeing her more regularly and began showing her, not only through his words but through his actions, that he was serious about her.
It goes to show that not everyone is a mind reader and knows what you’re thinking. As intimidating as it can be, relationships often require speaking up and sharing what’s on your mind when something bothers you or you need additional reassurance.
As with this situation, my friend’s communication was well-received and worked in bringing them closer together. Every situation is different, and communication can’t always ensure that someone will have to capacity to give you the answer you hope for, but regardless, it will bring you one step closer to the person who is a great fit for you.
4. Remind them of their best qualities.

When we have feelings for someone, it’s easy to base our value off of how that person perceives us—instead of remaining true to ourselves. It can be tempting to lose yourself in order to try to keep someone else.
I think back to one of the earlier heartbreaks I’ve had in my life. While I can look back now with gratitude, thankful for the lessons I’ve learned, I would have had a harder time getting there without a strong support system.
One of my closest friends knew I was struggling at the time, so she decided to take matters into her own hands. Unprompted, she reached out to me and began sending several messages with no context. The messages simply listed some of her favorite qualities about me: “You light up any room; you accept me as I am; your positivity is inspiring.”
At first, I was taken aback by her thoughtful and unexpected gesture. I responded to her with confusion, “What is this, and what’s the catch?” She “liked” my message, but she still didn’t provide an explanation. Instead, every day for the rest of that week, she sent me a simple text stating another quality that she appreciated about me: “You’re a loyal friend; you appreciate the simple things, you make me feel loved, etc.”
Finally, by the end of the week, I couldn’t take the anticipation anymore. “Seriously,” I asked her, unnerved by her random acts of kindness. “What’s this all about, and do you need me to bail you out of jail?”
With a smile on her face, she laughed and finally explained her rationale: “I wanted to remind you of the things I love about you for whenever you need them, so you can get your validation from within instead of from the outside.”
“I wanted to remind you of the things I love about you for whenever you need them, so you can get your validation from within instead of from the outside.”
It was so simple and yet one of the most selfless things someone has ever done for me. She had no motive, no agenda, no opportunity for personal gain. All she wanted was to put a smile back on my face and remind me of the aspects that made me unique.
It’s often easy to let others define how we see ourselves — especially when we’re trying to impress someone or feel the need to prove our worth. But with people who love you by your side, they can remind you of what makes you special, so you can remain true to who you are and be your most authentic self.
5. Applaud them for their courage.
Putting yourself out there, regardless of the outcome, takes courage. After all, it requires vulnerability to open yourself up to a potential connection — especially when that means admitting feelings or sharing parts of yourself that you usually wouldn’t.
Often, we only consider a date a success if it results in more dates — or if we advance from the stage of “dating” to “relationship.” But instead, we should shift our mindset. I think that any date going on is worth celebrating and a big pat on the back. With each one, you’re learning more about who you are, what you bring to the table, and what qualities you’re looking for in a future partner.
No matter what, you’re building up experience, gaining self-confidence, and realizing that you don’t need anyone to complete you, only complement you. That’s why dating, in my opinion, is never a waste of time. You’re investing your energy into finding someone who could become a big part of your life — and you should be proud of your initiative in looking for the person who is right for you.
The good news is that if a date goes well, then you have a new connection you can continue exploring with. And if a date doesn’t go as expected, then you still have a great story to reminisce over. Regardless, I like to remind my friends that I’m proud of them and that the journey is a worthwhile one, no matter where it leads.
As you can see, supporting others in dating can have a positive impact on their confidence and feelings of self-worth, particularly when done from a place of caring.
Contrary to what it might sound like, my version of being a “hype person” isn’t all about building unrealistic expectations or putting pressure on others’ dating lives. And it’s not about projecting too far into the future or promising them that the waters will always be smooth-sailing.
It’s about helping the people you love feel secure in themselves and what they have to offer. It’s about showing them your genuine support and reminding them of the attributes that make them special.
As for that friend who I supported at the nearby restaurant? Her date asked her out again. And eventually asked to make things official. Was it because I happened to be at the restaurant next door? Unfortunately, I can’t take much of the credit — it was all her warmth and charming personality. But sometimes, being a hype person pays off in the end.

 

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