Rachel Zwell | April 27, 2016

Matchmaker, Matchmaker?
Avoiding the Awkward
First Date

At some point in our dating lives, all of us have run into “the great fixup.” Whether your aunt works with a cute single guy or there’s an awesome girl who happens to live in a friend’s building, if you’re on the dating scene you’ve certainly heard, “So, I know this person who I think would be perfect for you…” at least once or twice.

Awkward first date alert! Right? Well, maybe…

If the thought of being set up makes you cringe, that’s totally understandable. Dating setups can feel awkward and uncomfortable. If your friend sets you up, there may be some unintended feelings of obligation. You may feel that if it doesn’t work out, things might get even more uncomfortable further down the road. Now that you’ve taken a dip in your own social pool, you may even imagine awkward post-date encounters at a friend’s dinner party or get together—so cringe-worthy!

But it doesn’t have to be that way!

It’s time to get past all that awkwardness. It’s time to rethink the fixup.

Fixed Up By a Friend: Is It Really So Bad?

Let’s reframe. If you use an online dating service like Tinder or OkCupid, you’re essentially trusting an online matchmaker. But think about it: Would you really put more stock in an online personality test than in a trusted friend’s matchmaking abilities? I know, I know, it does depend upon the friend in question. Maybe your matchmaker friend isn’t the “Fiddler on the Roof” variety, but if you’re open, honest and authentic with your friends in your everyday life, they’ve probably seen you at your best and at your worst—so they just might be able to successfully set you up. It’s worth a shot.

Yes, you might feel vulnerable or just plain weird when you give your friend the OK to make an introduction. Just remember: good friends will typically suggest someone aligned with your values, who wants the same things out of life you do. Hey, your matchmaker friend doesn’t want to make things uncomfortable either! Yes, there might be hits and misses, but chances are, the Venn diagram of shared social circles isn’t a bad place to look for possible connections.

Birds of a feather flock together, so you and that “friend of a friend” will probably have some similar interests and compatible personalities. Not only that, but your friends might already be past the initial “tall dark and handsome” first impression, so they can help you see into the deeper, more meaningful stuff of great relationships.

How To Turn Any Awkward First Date into Fun Experience

First of all, shake off the mindset that a dating fixup looks pathetic or desperate. Most of us pride ourselves on our ability to engage with others and we enjoy the idea of meeting new people. But whether you enjoy meeting new people or not, anyone can have a hard time asking for a fixup or accepting a dating setup from a friend.

But dating doesn’t have to be awkward! Try this…

Instead of looking at your fixup like an inevitably awkward first date, think of your upcoming encounter more like a business networking opportunity. At a business networking event, you often express your values, engage in conversation, and try to find commonalities to make a connection. Many of us go into business networking conversations with the hope we’ll find someone who shares our positive intentions and is looking to elevate themselves and grow in a business sense. We want to meet new customers, clients and peers who are going to build our business network.

In dating, your approach doesn’t have to be any different. In fact, the importance of approaching your date with curiosity and openness can often be even more vital in a dating setting, because it’s about more than just “making a sale.”

You can even look at dating as a whole in this way! Have you ever been approached by a business contact with an invite for coffee or a request for an introduction? Of course. But have you ever thought that person to be super-lame for asking? Of course not! Because when we’re approached to make a connection in the business world, it often comes naturally.

Think of your dating life in the same light.

Treat dating like an awesome playground! It’s a chance to really meet new people, engage with others on a new level, and grow as a person as you experience your reactions and interactions with a myriad of different people in a bunch of different settings.

So if there’s someone who seems interesting to you and you’d like to know more, by all means GO FOR IT! The worst that can happen is you’ll meet someone who’s not exactly a love connection—but now you can add another person to your connections and network.

When YOU’RE the Matchmaker

What if the tables are turned and YOU have the chance to play matchmaker or give advice to a friend? Interestingly enough, when we receive unsolicited advice, even when it’s well-intentioned, most of us rarely listen.

When we train coaches and undergo leadership training, we learn that most of the time “giving advice” should generally be avoided, even if it’s wonderful advice. Most people need to be steered toward finding the answer on their own. So keep that in mind when you’re advising your dating friends: you can’t argue them into the direction you want them to take or push them into dating a person you think they’d be perfect for.

Instead, put the idea on the table and help your friend seek out their own direction and answers. Similarly, if you’re trying to figure something out, look for those who have similar goals and who are working toward the things you want. Ask them how they got there and follow your own epiphanies.

What works for one person may not work for another. There’s no set red flags when dating and there’s no rules—a deal breaker for you might be just fine for another person. Instead of applying a set of “rules” or limiting your interactions because you’re trying to follow a specific path, allow yourself to work within the here and now. Keep a growth mindset and approach each situation as a learning opportunity.


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Rachel Zwell is one of the core coaches in the Year of Transformation program. She is an emergence coach specializing in empowering individuals to increase their fulfillment and satisfaction in their lives, to achieve their professional and personal goals, and to develop their leadership skills. She coaches and mentors people to develop self-awareness, vision, strategies, and to build skills in social and emotional intelligence. She believes in full engagement and aliveness, and trains people to see and overcome the barriers that prevent them from living fully.

Featured blog post image “Stops for a while” courtesy of Flickr user Seika licensed under CC by 2.0. The original image was altered for this use.

Wright Living is a division of the Wright Foundation for the Realization of Human Potential, a leadership institute located in Chicago, Illinois. Wright Living performative learning programs are integrated into the curriculum at Wright Graduate University.