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Why Is Dating So Hard?

Why Is Dating So Hard?

She plopped down in the seat across from me with a heavy sigh. Two weeks, four dates yet seemingly no progress toward a significant relationship. She was putting herself out there, making good conversation and doing all the “right” things. But with Mr. Right still nowhere on her radar, she was starting to feel disillusioned with the whole dating thing.

It’s a feeling that many of us can relate to, especially if you stayed in the dating scene for much of your 20s. We hear it all the time: “Relax! Dating is supposed to be fun! Just be yourself!” But after a long line of dates that lead nowhere, it’s hard to maintain a positive perspective and even harder not to go into a first date with a tiny bit of skepticism.

In his recent book, Modern Romance: An Investigation, author and comedian Aziz Ansari interviewed hundreds of singles about their dating and romantic lives. After asking specifically about online dating and apps, Ansari observed that a resounding theme emerging from most respondents was that they were tired.


The generation who is promised a date as easy as swiping right is worn out by the dating process. So when the disappointment and fatigue start to pile on, what is our next step? How can we encourage our single friends who are interested and open to the possibility of romance but feeling exhausted in the process of getting there?

Stop giving out meaningless advice

I think our first step is to resist the temptation to slide into comfortable advice and adages that we’ve heard a million times: “It’ll happen when you stop looking.” “There are a million fish in the sea.” “Don’t be so picky.” The list goes on.

Whether applied to ourselves or to others, these cliches can add pressure and more importantly, a sense that the single person must be doing something wrong. At the end of the day, after a date that goes flat or a romantic interest who never texts us back, words like these leave us with a lack of empathy and a fair amount of self-doubt.

It might be some of these ideas and expectations that are contributing to our world of weary daters. Let’s instead lean into opportunities to listen and encourage our single friends, and to seek out truth and healthy, wisdom from people who love us when we are single and feeling discouraged.

Put less pressure on yourself

A second step is understanding that finding someone to build a meaningful relationship with, and then actually building that relationship, is a process, like so many other long but worthwhile processes. We put a lot of unnecessary pressure on our shoulders (and on our dating prospects) when we believe that romance and relationships should be an instantaneous, magnetic attraction to our one, true soulmate.

Relationships with other people are never as simple, quick and clean as we would like for them to be. We don’t say to a woman who is 20 weeks pregnant, “Well, shouldn’t you have had your baby by now?” Of course not, because we understand that pregnancy and birth are a long, arduous process.

We need to remember the same thing about dating. It’s a process and a journey, and there is a lot of meaning and growth to be found in the process. Let’s be encouraged and encourage one another by looking for milestones and truths that are experienced along the way.

Remember that dating is unpredictable

There is no perfect formula for creating or finding love. So we can stop hustling and give ourselves a break from over-analyzing what we are or aren’t doing right. There’s no checklist or how-to book anywhere that is going to give us all the answers or a guaranteed outcome. And even though sometimes we would probably prefer that, we can find hope in knowing that God is crafting a unique story in our lives. It’s a story that will never be duplicated in anyone else’s life, and it’s our role to play in bigger story that He is telling.

The journey that we’re on may not be the one we expected and might not even be the one we always want. But sometimes, these tiring journeys ultimately lead us to places we couldn’t have imagined. So let’s offer one another grace and a little extra encouragement in the process, knowing that we’ll experience some losses and some victories, even as we keep our standards high and seek to honor God in the way we date. When we do that, we can rest in the hope that God is leading our steps along the way, and even more, that He is changing us in the process.

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