Why Dating Has Always Felt Like Work


By Tiffany Sun

I never thought I’d go on a casual date again until the worst thing happened to me.

“Tiffany, how would we know if we’re the “one” for each other if we’ve never given other people a chance? We should try dating — give it a year or so," said my ex of over 9 years.

As much as I tried to hold back tears every time I saw him busily texting another girl, I knew I had a new quest—to find a partner who would actually care about my feelings, love me as I am (including my imperfections), and appreciate every little thing I give him. It was a quest I didn’t want to go through but knew it was my best option for the future.

The most pressing matter was where to start. How do people find their potential partner if they’re no longer in school? Don’t have a job? Or have isolated themselves from their friends for years?

Match. eHarmony. OkCupid. Plenty of Fish. MeetMe. Skout. Tinder. CoffeeMeetsBagel.

I’m not proud to say that I’ve been through them all because ultimately I got nothing, except a reminder to self that maybe I should just call it quits. But knowing I had a 5% chance of finding my soulmate online pushed me to really try and make things work out with my dates.

But man, let me tell you, dating is tiresome work. It's like prepping for a big interview, not just for tomorrow but every day. That means knowing everything about the company (in this case, your date) before the first meet-up. Spending an extra hour to find the right outfit. Preparing a list of backup topics in case the conversation halts to an awkward silence.

If you’re new to dating, you might not feel that way. I have to admit that it’s all fun and games on the first few dates. That all changes once you start realizing you've wasted your day on someone who doesn’t seem like your ideal match. At that point, dating starts becoming a checklist.

1. Filter out who you want to meet.

26–34 years old?

Got a college degree?

5'7 or taller?

A serious foodie who’s addicted to milk tea and feels guilty if he skips the gym for three days straight?
Check, check, and check.

When there are thousands of options right at my fingertips, I use whatever filter that’s offered to narrow down my choices to my ideal partner. You might think I’m shallow, but for me, these qualifications mark the first sign of attraction.

2. Evaluate the quality of the conversation.

10 text messages. That’s all it takes to immediately know what kind of person he is.

  • How he sounds in real life.
  • How talkative he is.
  • Whether he is more approachable or more reserved.
  • How long he can keep a conversation going.
  • How serious he is about dating.

The more I talk with him, the better I can make a judgment on whether it’s worth my time meeting him.

Of course, there are times where his quality comes cheap especially when he’s got a plentiful list of people to talk to. If that’s the case, I avoid being desperate and move on. I mean if he doesn’t make the effort to talk to me seriously, why should I?

But if I really enjoy talking with him to the point where I start missing his presence when he’s offline, I jump to the next step.

3. Schedule a time and place to meet.

Usually, in my social life, I go along with other people’s suggestions, which makes this step incredibly stressful for me.

For one, I need to know what my date is interested in. Is he into Korean food? Does he like working out? Watching movies?

Next comes the delicate dance of figuring out the best time for us to meet up, one that's convenient for both of our schedules. Hmm, he works from Tuesdays to Saturdays. He takes jiujitsu classes from 6–8 pm on Sundays. He’s attending a birthday party in the afternoon on Monday.

In about 90% of my cases, it ends up being coffee in the afternoon or dinner at a nice restaurant, which I deem as the “safest” choice for the first date. If the date turns out better than I expected, I expand my options to hikes, movies, festivals, or a stroll downtown.

4. Be clean. Dress nice. Smell good.

The last thing I want is to turn off a date with bad hygiene or not looking put together. That’s why I always spend an extra 30 minutes to an hour getting ready just to show him that I care about myself (it’s worth it if he’s a good catch!).

5. Look back on his profile before the big date.

I always, always reread my date’s profile and our conversations. This is important because I’m pretty forgetful of what guys have said to me, especially when I’m chatting with more than one guy.

Me: So when is your brother moving to Los Angeles? He must be pretty stoked about living on his own.

Him: I don’t have a brother. Just a sister.

Me: Oh…what was I thinking?! …sorry, I’m totally out of it today. *nervous chuckle*

Total fail.

Moral of the story? Save yourself the embarrassment (and possibly his growing suspicion of you dating multiple people) by going over his entire profile.

Remember to take a good look at his profile picture too, so you don’t accidentally shake hands with a stranger.

6. Read his mind and body gestures, constantly.

As much as I want to drop my guard and just enjoy his company, I can’t.

I remember how my first date tried to feel my shoulders after I told him I grew up with big bones from consuming too much milk as a kid. It gave me instant chills right down to my spine. Since then, my mind has always been on high alert on every word my date says or move he makes.

But in order to move things forward without being too forward, I have to constantly think about what he’s thinking and analyze his body gestures before responding in a manner that I feel comfortable with. It’s tough because while I do want to move forward and get to know him better, I need to keep an arm's length away from him. I don't want dates making a physical move on me when I’m not ready.

7. Invest a ton of your time and attention to maintain the relationship.

If he passes the first few dates and things are looking pretty positive between us, I put in more effort to talk to him. Texting. Emailing. Calling. Face-timing. It didn’t matter what channel I use, what matters more is getting to talk to him at least once a day, even if that means texting a dozen messages in response to yesterday’s chat.

Eventually, it becomes less forgivable to go a whole day without talking to him. By then, he has an unhealthy suspicion that I might be with somebody else.

But no, I’m only chugging away at work, giving myself some ‘me’ time, or catching up with friends. Just finding some balance in my life. Yet I can feel his vibe, it's one filled with doubt and dishonesty. He's questioning my commitment to making the relationship work.

At that point, I feel like I'm left with two choices. Either I sacrifice my work and personal time to make more room for him in my life, or I s tart back at the top of this checklist.

Actually, that leaves me with only one choice.

writer photo

Tiffany Sun

Creator & Marketer of Rabbut - a writer's best friend for collecting emails for Medium, Linkedin, and personal sites. Top Medium writer for life hacks, productivity, startups and relationships.