Managing Expectations When You’re Beginning to Date Someone

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Manage expectations

(phrase of expectationSeek to prevent disappointment by establishing in advance what can realistically be achieved or delivered by a project, undertaking, course of action, etc. (Oxford Dictionaries)

YK thanked me for managing his expectations when I was making dinner plans with him in Singapore. I had warned him that I was severely jet lagged, and that I probably wouldn’t be that much fun. It wasn’t that I was telling a white lie and actually didn’t want to hang out with him – I honestly just wanted to set his expectations straight. The concept got stuck in my head, and it struck me how complex of a maneuver it actually is. Breaking it down, you need to:

  1. Understand what the other party is expecting
  2. Understand what you are willing and able to offer
  3. Communicate the mismatch between expectations and reality

In this scenario, I understood that YK: a) wanted to spend quality time with me since I rarely visit; b) I have been crashing around 5-8 pm. All that was left was to tell him tactfully: c) “Just to let you know, realistically we’ll probably only get to hang out till 5 or 6 pm.”

I started thinking about how this concept applies to dating, especially in the early stages when you haven’t quite figured out how to be open and honest yet. It is an incredibly elaborate dance of not being presumptuous while not wasting anyone’s time or hurting anyone’s feelings (if you want to be a good person, at least). Although managing expectations connotes that you are the one doing the disappointing, I believe it’s also about being empowered to convey your expectations.

1. Understand what the other party is expecting

I’ve found that the best way to suss out someone’s intentions is to always be on the pulse in observing his behaviors. Unfortunately, there’s no universal threshold of behavior that definitively suggests if he really likes you or not. How he expresses love (or his love language) is going to be different from yours. Your baseline is going to be different from his baseline. Just because he texts you a lot, made you a smoked salmon omelet the first time you sleep over, or spends his precious Saturday night with you still doesn’t mean he wants to be with you. Maybe he likes you a little bit, but maybe he also feels lonely and misses being in a relationship. Maybe he seems aloof and cold at first, but simply takes a longer time to warm up to someone new. Events out of our view may be affecting his behavior. How nice or how standoffish someone is with you is often less about you than you think.

One thing that has helped me be more observant about my date’s behaviors is to worry less about how I’m being perceived and instead keep the focus on him. It’s too easy to ignore the signals you’re getting if you’re too caught up in your own mind. It’s easy to forget that you are judging the situation as much as you are being judged. Having a good grip of the value you bring to the table enables you with the confidence you need to laser focus your attention on him, and not the mistakes you think you’re making.

2. Understand what you can offer

Ah, self-awareness. How do you actually feel about someone? What are you ready for? What do you want to offer? Maybe you feel blase because there isn’t excitement that you’ve once felt for your ex. Maybe you’re nursing a heartbreak from not too long ago and you find all these reasons to discount someone new but none of them are actual red flags or deal breakers. Don’t dismiss someone just because there isn’t an immediate spark. I’ve realized that the most passionate beginnings don’t always lead to long-term, sustainable relationships. The fact that both of you are keeping it going despite there not having been an agreement or a furious passion indicates an interest to keep it going, which is all you need in the early stages of a relationship. Sometimes the inexplicable desire to keep giving someone a chance is enough.

At the same time, you don’t want to keep going with the flow when there’s no end in sight. Maybe you’re tired of the stasis in the relationship. Maybe you feel like your needs aren’t being met. Maybe the guy checks all the boxes but something doesn’t feel quite right. Feeling obligated to your shared history and a fantasized trajectory should not be a big factor when you’re just beginning to date someone. Things change. Situations evolve. Consider the here and now instead of the past or the future.

3. Communicate the mismatch between expectations and reality

When you are tired of guessing and hinting, that’s where a conversation has to happen. There are several points where this may need to happen, sometimes out of pure utility. Maybe it’s after you’ve first had sex and you want to make sure you don’t get diseases or a baby.  Maybe you see a Tinder message pop up on his phone and you wonder if you should recalibrate your expectations of the relationship’s trajectory. Maybe you realize you can’t give him what he wants. Or maybe you’re really in love and you can’t bear it any longer.

But you fear that you lose the person whose attention you’ve managed to hold or the person to whom your attention is worth everything. But at what cost? Are you being good to either of you by maintaining the unspoken status quo? However, while I don’t want to operate on assumptions, I also don’t want to call the fate of a relationship and when it’s too early to be called – relationships have bent one way when I thought it was going to bend the other. I don’t want the dating to be dominated by discussions of the relationship than actually just being in one. But if push comes to shove, tactically, using “I” statements while leaving the discussion open-ended has worked out the best for me. “I feel (feeling) when you do (action).” – that’s been my favorite template.

Good: “I feel really confused when you are really touchy to me in private but barely text me when we’re apart. I really like you but it seems like maybe you feel differently. What’s going on?”
Not good: “You’re being very cold to me. Are you seeing someone else?”

Good: “I feel like I don’t have enough time to do my own thing when you want to hang out all weekend.
Not good: “God, you’re so clingy!

This means not making accusatory “you” statements which attribute intent. The goal is to seek truth in the most tactful way possible, not impose your viewpoint.  It also means making your respondent feel comfortable about saying something that could possibly upset you, and assuring him that you don’t need finality. Of course, be prepared to hear things you don’t want to hear, and be prepared to not get an answer right away if you’re springing this game-changing conversation on them. You’ve had time to mull it over while they haven’t.


I staunchly believe that Tom and Summer in 500 Days of Summer could use a good expectations-managing conversation. Watching that movie is always a little agonizing for me – I just want to shake them by the shoulders and ask them to wake up.


The Author

Singaporean in NYC, analyzing relationships with a boozy brownie in hand.

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