9 Things to Never Do in the First Month of Dating: A Guide

Jun 24

The people I work with are exceptional at almost everything. They run teams, close deals, manage portfolios, and make hard decisions under pressure for a living. Then a promising new relationship reaches its first few weeks, and the very instincts that built their careers quietly start working against them.

I come at this from two directions. I spent years in investment banking at Goldman Sachs and JP Morgan, so I understand and saw how these high performing professionals work …and play. And I’m a third-generation matchmaker — my mother and grandmother were both 紅娘 — so I’ve seen, across a lot of introductions, the same pattern of avoidable mistakes end connections that were starting out.

Don’t miss these cues. How you start a relationship impacts balance and boundaries and the success of a partnership.

1. Never turn the date into an interview

Smart, accomplished people love metrics and evaluation. It works in school and education and in the workplace. So the questions come out like an interview or job screening: What do you do? Where did you study? What are you looking for? It feels efficient, and it kills the evening. You get rehearsed, surface-level answers, and the other person feels assessed rather than met. A recent client - in a hedge fund - was responsible for recruiting at his firm and he thought it would be a good idea to use these techniques when going out on dates. (wrong)

Trade the résumé questions for one small word - ask questions that show interest and curiosity - for example - You like hiking? What do you actually love about it?” Not “What do you do,” but “Why that field?” “Why” pulls people out of their script and into something honest — and give your date the opportunity - and safety - to share without judgement.

2. Never mistake the spark for a verdict

That electric first-date feeling is real, chemistry is fun - but it’s not always evidence. Novelty lights up the brain’s reward system. A little first-date nervousness raises adrenaline, which we routinely misread as attraction. And sometimes “chemistry” is just familiarity — someone who reminds you of a pattern you already know, not someone who’s right for you. Chemistry also can come from being truly seen by your date - that open-minded curiosity is the long lasting spark.

None of that means ignore the physical spark. It means don’t hand it the final say in week one. The qualities that actually sustain a relationship — consistency, steadiness, how someone shows up over time — are not automatically shown on a first date. There’s a reason why we often suggest 3 dates.

3. Never argue with what they tell you they want

This is the costly one. Someone tells you — directly or through their profile — that they want something casual, that they’re “not really looking for serious right now,” that they’re still figuring things out. And because everything else lines up, you decide to treat that as a detail you can change later. People generally show you themselves but it’s up to you to see it.

You can’t change someone - only they can. When you invest in someone’s potential while they’re being honest about their present, you’re the only one operating from a different set of intentions — and it ends the same way nearly every time. Take people at their word the first time they show it to you.

4. Never keep one foot in the app

More options feel like leverage. They’re usually the opposite. When you’re still actively browsing, comparing, and “keeping things open,” you stop investing real attention in the person actually in front of you — and they can feel it. The endless-options mindset that helps you optimize a deal will erode a new connection. There are numerous studies discussing how people that meet on apps feel less connected with their dates and if something does not work out - a bump along the way - they more easily revert back to the apps to swipe some more for another date. That’s not valuing the person.

For the first few weeks with someone promising, narrow your focus to one or two people and give it a genuine chance. Connection isn’t built by maximizing alternatives, and looking for the next opportunity. Truly see who you are dating.

5. Never lead with your résumé

Many people can bring their work persona on a date and lead with a resume of their accomplishments. While we are all justifiably proud of ourselves and what we’ve done in work and we sometimes try to present an outward face - showing the most impressive version of yourself early — the achievements, the travel, the credentials. But is that to satisfy your own need? Does that create attraction and connection or…inadvertently now adding a barrier. How does your date feel? Think of it this way - what is the purpose of sharing that?

The simplest, most attractive thing you can do in the first month is be a little more human and open-minded. Share a funny story or a childhood memory. If you and your date ended up being partners what is your life going to be like? A resume of achievements or a life together building family and fun and adventure.

6. Never read a slow reply as rejection

High achievers are used to fast, legible feedback. Dating doesn’t run on that - there are emotions involved. When someone takes a day to text back, or a plan slips, the anxious response would be “I did something wrong.” Usually you didn’t. People have lives, busy weeks, and their own nervous systems to manage. What you put out impacts what you attract back. Confidence is attractive. Anxiety is not.

And when someone genuinely does pull back, it’s far more often about their timing than your worth. You can’t think, fix, or perform your way into someone else’s readiness. So instead of spiraling on “Why wasn’t I chosen,” ask the cleaner question: was this person actually available for what I want? That keeps your footing under you and staying grounded.

7. Never carry the entire relationship yourself

If you’re proactive and capable — and you are — it’s easy to quietly run the whole thing: planning every date, carrying every conversation, smoothing every pause. It feels generous. But it removes the other person’s chance to show up for you, and effort that only flows one direction rarely turns into lasting attraction.

Don’t ignore your own friends and life to make things work out in your initial dates. It’s a partnership.

Leave some space. Let a silence sit instead of rushing to fill it. See whether they move toward you. The right person will meet you with equal energy — and you want to know early whether they will.

8. Never rush the pace to lock it down

When something feels promising, the optimizer’s instinct is to accelerate — long marathon dates, constant texting, fast talk of the future — as if commitment can be secured through sheer momentum. It usually does the opposite. Anticipation and a little space are part of how attraction builds; flooding the early weeks flattens both.

Keep the first few dates shorter than you think you should — sixty to ninety minutes that leave you both wanting more. Let the relationship find its own pace instead of forcing one. Something real doesn’t need to be rushed into place.

9. Never ignore how they treat people who can’t do anything for them

You’d never hire someone on the strength of their résumé alone — you’d watch for consistency between what’s on paper and who actually shows up. Apply the same discipline here, and not to how they treat you. Watch how they treat the server, the valet, the person who makes a small mistake. Watch how they handle a minor disappointment when the night doesn’t go to plan.

Those unguarded moments tell you more about the next ten years than any answer to a direct question will. Character shows up in the margins. Pay attention to the margins.

The real throughline

Almost every mistake on this list comes from the same place: treating the first month as something to win, optimize, or get right. It isn’t. It’s a period of discovery — a chance to find out, with clarity and a little patience, whether the person in front of you fits the life you’re building. Use that clarity as a tool, and the early weeks get easier, not harder.

That’s the difference between dating reactively and dating with intention — and it’s exactly the shift the people I work with are looking for.

two women having fun together — Friendships are to be nurtured

Maintaining individuality and personal space is crucial in new relationships. Being overly available can create an unhealthy dynamic.

Matchmaker Cassindy emphasizes the importance of balancing dating with personal life. Continuing regular activities and hobbies is essential, and remember that independence in a new relationship can strengthen the bond.

Why Stop at 9 things….Here are a few more just because!

Avoid Unrealistic Expectations

So, listen up - It's important to distinguish between fantasy and reality in new relationships. Idealizing a partner can lead to disappointment. Movies and stories always talk about being swept away by someone. My 2 cents there - easy come, easy go. That’s in our own head and not what makes a true relationship work. Focus on how your date makes you feel and seen. Bragging rights are not realistic and that gets stale sooner than one thinks. AWM Love recommends setting realistic expectations.

Unrealistic expectations can adversely affect relationship satisfaction. Navigating the fine line between hope and practicality is the key to starting a healthy and happy relationship.

Avoid Introducing Them to Family Too Soon

Introducing your new partner to your family is a significant step. In the first month of dating, it's often too soon for such a big move. Early family introductions can bring unnecessary pressure. AWML recommends waiting until both partners feel ready and the relationship is more established.

Balancing your own personal desire with the relationship's readiness is critical since premature family introductions can alter the natural development of the relationship dynamic. Give your relationship time to develop and strengthen without the pressure of curious family! And I know, as a parent of three young adults - the sheer curiosity yet it’s important that we all individuate.

If you want to learn more about navigating the world of dating, make sure to check out the AWML blog here.

Don't Plan Too Far Ahead

In the first month of dating, it's essential to avoid making long-term plans prematurely. Jumping ahead can create unrealistic expectations. Focusing on the present allows you to understand your partner better.

AWML emphasizes the importance of gradual progression in relationships since rushing into future plans can put undue pressure on both partners and the spontanaeity of a strong and healthy partnership.

It's beneficial to enjoy the current dating phase as this phase is crucial for laying a strong foundation for what may come next. Savor these early moments without the burden of long-term expectations.

Refrain from Social Media Overexposure

In my book, I share a chengyu - and how a relationship is like a painting. There is a famous Chinese phrase about “Painting the Dragon and Dotting the Eye”. It is about a famous painter who drew an elaborate dragon and at the end dotted the eye and the dragon comes to life and flies away. A relationship takes time to develop, but pace it and when it blossoms your relationship can take flight and you both can soar to great heights and adventures together.

If you’d like to work with us on your own love story reach out - we’re ready to chat with you. LINK: Chat with Matchmaker Cassindy

cassindy chao