An Introvert’s Approach to hookup Dating

I’m going to get personal for this post, not because I think anyone really cares about my personal life, but because I don’t think my story is all that unique and maybe someone out there can find something useful.

The Challenge

As difficult as dating is for everyone, it’s harder for people who, like myself, have some natural tendencies towards introversion. Yes, this includes all you shy people, but I’m also referring to people for whom the superficial social interactions are incredibly draining. The ones who after enduring forced socialization want nothing more than to hibernate in a soundproof room with a good book and a cup of hot tea. If you fall anywhere on this spectrum, dates aren’t just pointless, they can be painful. Simply put, dating is draining.

Introverts don’t necessarily have a problem with forming intimate relationships, but genuine closeness takes time and trust. As hard as this is to achieve in the real world, it’s even harder in the hookup dating world, especially in the Orthodox community where the social emphasis on the “tachlis” – the end-goal of getting married – means fewer opportunities for developing close friendships. Dating often implies an immediate commitment, which in turn puts many introverts on the defensive. After all, how do you know that this person you just met is worthy of your trust, vulnerability, and the general effort it takes to foster a relationship.

On top of all of this, I personally faced additional challenges as a congregational Rabbi. I’ve had countless conversations with people over coffee or tea – I joked the Starbucks on the corner of Delancey and Allen was my real “office” – and I truly enjoyed connecting with everyone. I’ve learned I can talk to anyone about almost anything, and possibly even enjoy it in the moment. But, the dynamics between a Rabbi and a congregant are different from that between two people who are dating (or so we’d hope), and it became harder for me to turn the “Rabbi mode” off, especially when meeting a random stranger for the first time. The end result was that even if I could share a painless or even pleasant few hours with anyone, after a while I couldn’t tell the difference between dating and working. This became unfair to the people I was dating and unhealthy for me to continue.

Basically, it was time for a change.

The Strategy

If the above sounds like burnout, you’re probably right. And if you’re an introvert, you’re not alone in feeling this way from time to time. One solution to this problem is simply to take a break from dating. This is a decent possibility in the short term, but unless we modify future behaviors, we’re only delaying the next inevitable breakdown.

Instead of just taking a break, I also made a conscious decision to curtail my dating entirely. When I first started dating I would go out with anyone who was suggested without asking too many questions. This approach not only didn’t get me any closer to finding someone, but it pointlessly consumed time, money, and energy. Gradually I started saying “no” to more suggestions, and only accepting or pursuing the people whom I actually wanted to date. My goal was to take on fewer dates which felt like obligations in favor of social interactions I’d find enjoyable.

It turns out I had unknowingly been practicing what Greg McKeown calls, “Essentialism,” a mindset which emphasizes “less, but better.” For McKeown, any decision we make involves a tradeoff, but if we don’t make decisions for ourselves, someone else will make them for us.

By definition, applying highly selective criteria is a trade-off; sometimes you will have to turn down a seemingly very good option and have faith that the perfect option will soon come along. Sometimes it will, and sometimes it won’t, but the point is that the very act of applying selective criteria forces you to choose which perfect option to wait for, rather than letting other people, or the universe, choose for you (105).

To put Essentialism in context, consider all those times you went out on a date when you really didn’t feel like it. Maybe you got pressured by a friend, family member, or shadchan. Maybe it was that nagging voice in your head that you have to keep trying and, “you never know.” These are choices to be sure, but these choices aren’t made by us as much as imposed on us. Either through social pressure or the guilt associated with the fear of missing out. These are the sorts of forced social interactions many introverts dread.

And what about that fear of missing out? McKeown suggests trying a “reverse pilot” in which we experiment with cutting out potential distractions and measure the consequences.

Are there commitments you routinely make to customers, colleagues, friends or even family members that you have always assumed made a big difference to them but that in fact they might barely notice? By quietly eliminating or at least scaling back an activity for a few days or weeks you might be able to assess whether it is really making a difference or whether no one really cares (154).

Of course the only person whose opinion ought to matter is you.

But the real point here isn’t selectivity for the sake of being a contrarian or out of ego. I don’t decline people because I think I’m above anyone or that I “deserve” better. And while the Talmud does not encourage refusing B. Yevamot 109b, the focus here is less about saying “no” to another person, but saying “yes” to everything else in your life.

But the way of the Essentialist isn’t just about success; it’s about living a life of meaning and purpose. When we look back on our careers and our lives, would we rather see a long laundry list of “accomplishments” that don’t really matter or just a few major accomplishments that have real meaning and significance? (230)

The Results

So how is all this “Essentialism” working out for me? Surprisingly well, though you have to look beyond the obvious.

The immediate response would be to see if my approach to dating has actually resulted in marriage. But it’s important to keep in mind that nothing else I’ve tried has resulted in marriage either. From this perspective, I’m still just as single as I’ve always been.

On the other hand, I’ve found myself to be a whole lot less bitter and frustrated. To some extent, this was simply addition by subtraction. The job of a Rabbi itself can be emotionally draining, often leading to its own type of burnout. Time spent with others often means time not spent recovering emotional strength. But it also freed up my time to pursue any number of interests. Instead of chasing down and forcing small talk with random strangers whom I’d likely never see again, I was free to do, well, anything else. I could read, write, practice guitar, go running, take up painting, whatever.

More importantly, while I’ve been going out on fewer dates, the ones I have been on have been more enjoyable. No one can predict how a date will work out, but on the whole, a nice simple night out is better than most alternatives.

All of this is predicated on the fundamental assumption that there can be more to life than getting married. If getting married is your primary goal in life, then yes, cutting down on dates might not be the best strategy and fellow introverts will just have to suffer the cost of doing business. But for the rest of us getting married – or more importantly having a good marriage – is only one part of living a happy and healthy life.

Deciding not to date because you want to stay at home and brood is probably not going to do you or anyone else any good. But choosing to live the best life you can on your own terms can bolster your quiet confidence and inner strength. Even if you still don’t manage to find someone – a very real possibility for everyone – you’ll still have the significant solace of living a life worth living.