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The Paradox Of Choice

Many singles try to date as many people as possible as to not miss out on meeting “The One," but this can lead to an insidious addiction.


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For ten out of thirteen years, I dated organically. I always met my boyfriends through friends or outings and we would date for a period of time. There were no distractions, and it was memorable. Sometimes I would meet someone by chance. We were both in the same place at the same time and lucky to bump into each other. It had a serendipitous feel to it all.

All of that changed in 2014. I had just broken up with my boyfriend. I was 28 years old. And I found myself directly in the midst of a whole new digital dating era. I decided to give Tinder and Bumble a whirl. I started dating in such an unfamiliar way –– dates based on a 2-3 sentence bio (or a slew of emojis). Rather than being excited about a date ––because it was probably my only date that month –– I felt overwhelmed and anxious by the number of dates I had to track via my google calendar. In the end, all of my dates were great, yet nothing materialized into a relationship for an entire three years. I kept asking myself, “Why is this happening?” “Is it me?” I used to love dating, and now I felt less than enthusiastic. There was no unanticipated, serendipitous encounter. It was all greatly anticipated, with the knowledge that if the date went south, there were other options waiting on my phone. Everything felt much less romanticized.

Recap –– Pre-online dating Taylor: confident, enjoyed dating, found successful relationships. Post-online dating Taylor: self-confidence shattered, doubted love, found a slew of first dates with 0 relationships.

The dating app trap –– the paradox of choice

I believe that whenever we start using dating apps, we all fall prey to the same problem – the paradox of choice. Let me give you an example… You just met someone off Tinder, or Bumble, or Hinge, or wherever, and the first date is going really well. You probably want to see them again. Then, your date ends, you walk outside, hail a cab, pull out your phone, and immediately pull up your dating app. If THIS date went so well, you just can’t help wonder who ELSE you might find. Maybe there’s someone just a little more successful, humorous, well-traveled, or well-read. This is what American psychologist Barry Schwartz defines as the paradox of choice. Barry says, too much choice causes the feeling of less happiness, less satisfaction and can even lead to paralysis.

The paradox of choice creates a real sense of anxiety for people looking to find a long-term partner. Many try to solve this problem by dating as many people as possible, as to not miss out on the chance of meeting “The One.” There’s two issues with this approach. First, the idea of finding “The One” is problematic in dating. The expectation that one person can satisfy our emotional, physical, and spiritual needs is unrealistic. Instead, remove the added pressure that he or she has to tick all the boxes and focus on a person with whom we can imagine ourselves writing a story that entails edits and revisions. (Remember, there are no perfect stories!) Second, as we just discovered, an overabundance of options can actually lead to anxiety, indecision, and dissatisfaction.

This is exactly what happened to me. I wasn’t following through with any of my dates because, with so many options on my apps, I thought that I could find someone that “ticked all of the boxes,” not just a few. I was inundated with a limitless stream of swipes, and when my thumbs fatigued, I relied on matches being pushed to me via email and text. With something as important as finding love, I wanted to be sure I tested all of my options before settling down for the rest of my life, right? However, with this approach, I could test my options literally for the rest of my life. I ran into decision fatigue and didn’t go on a single second date. I was tired, frustrated, and just gave up.

This doesn’t mean that dating apps are from the pit of hell. There is an upswing to having hundreds of potential matches at our fingertips, if we know how to navigate our way. It involves a mindset shift.

American Journalist Sebastian Junger once said, “The tricky thing about life is on the one hand having the courage to enter into things that aren’t familiar but to also have the wisdom to stop exploring when you have found something worth sticking around for. That’s true of a place, a person, of a vocation…”

It takes wisdom to know when you have found someone worth pursuing. And it takes courage to leave the noncommittal and casual world of dating and enter into a committed relationship.

How do we know when we have found someone worth pursuing?

The first date is for testing mutual attraction and chemistry. The second date should feel more comfortable since you both have established that there is a mutual attraction. With your guards lowered, conversation should flow more naturally and willingly. Then comes the third date. You scratched the surface, but now you want to crack it. You begin exploring your emotional and intellectual compatibility through more in-depth conversations. By this point, you start unraveling his or her quirks, habits, and traits. Ideally, by your third date, you should know whether you would like to continue dating this one person or cut ties. When deciding to move forward and date just one person, it should be for the right reasons. There should be chemistry, compatibility, and desire.

Read more on this topic: Romantic Chemistry Explained and Chemistry & Compatibility: What You Need To Know

Chemistry is the butterflies that flutter just before you see him, compatibility takes the form of a best friend; you share similar values and worldviews, and desire is a feeling that you must see the person again. Without desire, it’s pointless. Author Derek Sivers made an extremely simple but life-altering point in his book, Hell Yeah Or No. “If you’re not saying HELL YEAH! about something,” he says, “say no.” When deciding whether to do something, if you feel anything less than “Wow! That would be amazing! Absolutely! Hell yeah!” — then say “no.” When you say no to most things, you leave room in your life to really throw yourself completely into that rare thing that makes you say “HELL YEAH!” I’d like to apply this rule to dating.

When you aren’t saying “hell yeah” to the person you’re dating, and when they aren’t reciprocating a “hell yeah” to you, then say no and walk away. This will save you many future headaches.

You don’t need to be absolutely convinced that you are going to fall head-over-heels in love and marry this person. You just need to feel a “hell yeah” to getting to know this person. If you’re already in a committed relationship, you should feel a “hell yeah” to continuing the relationship. If you’re in a relationship and experiencing problems, you should feel a “hell yeah” to resolving those issues and continuing the relationship.

Author and Blogger Mark Manson writes a great article on this very topic. He strains the point that both parties should be equally as enthusiastic about one another and that no “grey area” should exist. This grey area is composed of ambiguous feelings and one having stronger feelings than the other. “If you’re in the grey area to begin with,” he says, “you’ve already lost.”

Manson points out, in his more explicit blog title “F*** Yes or No”, this rule has many tangible benefits on our dating lives, including:

  1. No longer be strung along by people who aren’t that into you. End all of the headaches. End the wishing and hoping. End the disappointment and anger that inevitably follows. Start practicing self-respect. Become the rejector, not the rejected.
  2. No longer pursue people you are so-so on for ego purposes. We’ve all been there. We were so-so about somebody, but we went along with it because nothing better was around. And we all have a few we’d like to take back. No more.
  3. Consent issues are instantly resolved. If someone is playing games with you, playing hard to get, or pressuring you into doing something you’re unsure about, your answer is now easy. Or as I often like to say in regards to dating, “If you have to ask, then that’s your answer.”
  4. Establish strong personal boundaries and enforce them. Maintaining strong boundaries not only makes one more confident and attractive, but also helps to preserve one’s sanity in the long-run.
  5. Always know where you stand with the other person. Since you’re now freeing up so much time and energy from people you’re not that into, and people who are not that into you, you now find yourself perpetually in interactions where people’s intentions are clear and enthusiastic. Sweet!

Dating one person at a time frees our mind and spirit to focus solely on that person. It creates space to get to know our date; his quirks, his interests, what makes him tick. This makes me think of my pre-online dating experience; times when I used to enjoy dating and learning about people; times when there wasn’t so much pressure to swipe my way to “the one.” I know now that we can relive these simple times in our digital dating era by implementing this one simple rule.

So, the real question becomes, when you meet someone worth pursuing, will you do just that?



Subscribe to the Date Smart Podcast

The Date Smart podcast is hosted by Ambiance Matchmaking’s cofounder Taylor Wade. Twenty years ago, Taylor cofounded Ambiance Matchmaking, an exclusive matchmaking agency that has helped over 100,000 singles master their dating lives. In this podcast, she shares the same tactics and techniques with you. Mastering your dating life is easier than you think –– it’s just a matter of science and a little know-how.

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Taylor Wade

Taylor is one of the founders of Ambiance Matchmaking. She now dedicates her time to curating content for our community through her podcast and blog. Writing and podcasting is the art of great story-telling. As a relationship writer and editor, she has always sought to capture the reality of the dating experience, full of drama, friction, and joy. The best mind is an open mind, so she specializes in asking questions and approaching a story without preconceptions.

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