Overcoming Modern Dating Challenges that are Unique to Gens X and Y

The rules of modern dating – as anyone who has ever entered the battlefield knows – are that there are very few rules. Or so it can seem.

It is true that things are a lot different to when our parents were dating. And it is also correct that we need to toughen up and have our shit together to survive the chaos and uncertainty (which just means being strong and secure in who we are).

The challenges that Millennials and Gen Z face in romance are unique by virtue of several reasons, but one main one: the possibilities for meeting people are exploded by online dating apps.

Online dating apps are fun to use and, in my view at least, positive overall for the connections that they make possible.

But with increased options come the sprawling possibilities for flakiness. The people we date might be dating several other people, or at least interacting with many others. And it can sometimes feel like there has been a loss of some basic rules of dignity, civility and respect. The fact that unscrupulous practices like ghosting are on the rise is evidence of this fact. 

This post offers a few experience-based suggestions on how to navigate the tricky world of modern dating, and maintain your sense of self worth in the process. (I’ll assume you already have some standards for the types of people you agree to go out on dates with.)

Coping with rejection early on: ‘the art of no contact’

Let’s say you have met a person that you quite like and are in the early dating phase. You think it is going well but then suddenly, you get the strong sense that a retreat or a change in heart has occurred. How to handle this?

Rejection has always, and will always, be a part of the relationship landscape. And rejection has its positives. But we get to choose how to respond to perceived rejection situations: a fact which we completely forget. 

A mistake I have often observed is that we freak out, becoming clingy and adopting a scarcity mindset about the person we are dating. We make them too special in our eyes. Partly, that response is driven by biology: for humans, what we can’t have is always heightened in value. 

Smart dating means being staying one step ahead of your brain biochemistry Click To Tweet

The only response to a change in behaviour of the person you are dating is to quietly disappear. If someone isn’t interested in spending time with us, then why on earth would it be appealing to argue with that in any way? It is so deeply irrational when you think about it.

Take refuge in golden silence. I think this alone has the potential to transform your experience of dating. It takes discipline to begin with, but everyone can do it.

Dealing with non-rejections

Rejection is one thing, but now we have ghosting, and icing and simmering too (definitions provided by Adam Devine below). We never had so many ambiguous endings before. 

Ghosting: Ceasing communications suddenly and entirely with someone you are dating but no longer wish to date.

Icing: Manufacturing a reason to suspend the relationship a la ‘I’m too busy’.

Simmering: Reducing the frequency of dates and communication.

Relationship expert Esther Perel says we create these states of ‘stale ambiguity’ because we are too afraid to be alone, but unwilling to fully engage in intimacy building. The resulting holding pattern has a mix of comforting consistency and the freedom of blurred lines. It’s all a bit pathetic really.

When we are on the receiving end of these, we can kid ourselves that the absence of a direct communication is somehow meaningful, and that the person we are dating is still into us and taking us seriously.

Being simmered should never be a remotely attractive option for you Click To Tweet

I would avoid this. Women all know when they are being pursued by a man: there is no mistaking it. Equally, men know when women are being genuinely responsive to them.

How to respond to any of the behaviour above is the same way you respond to a clearer rejection: by disengaging and moving on. 

The perils of ‘keeping options open’

So far this post has taken the perspective of the recipient. But I am sure you have not behaved like an angel yourself, as nobody does. And if we truly want to see standards raised in the way we are treated, then we need to raise our own standards. That means avoiding using ambiguous endings ourselves.

I think we can call understand why ghosting is tempting. Nobody wants to inflict the pain that a direct communication can cause.

If you use ghosting and other tactics, then that’s your choice. But I would simply question the longer term effects of playing the game you’re playing. Once you start using the lower forms of accountability with the people you are dating, you will undoubtedly receive the same treatment from other people. You’ll expect it. It is a universal law.

If you are into keeping your options open, question the long term effects of that game Click To Tweet

Aside from that, keeping your options open leaves no room for Mr or Miss Right to grace your presence. You end up with so called ‘place holders’. When a quality mate does finally present themselves, it is unlikely that you’ll be in the position to step up and claim them.

Power parting

Power parting – breaking up with someone in a clear way – is our passport out of dodge when it comes to bringing back accountability in dating scenarios. It is rare because a person as to be very secure in themselves to do it, and most of us aren’t that secure. 

If you know that you tend to keep options open, develop more trust in the future, and finally learn that you do not need to compromise or settle in case nobody else comes along. Learn how to be alone. It’ll serve you in the end. 

How to filter people early on

Okay we have handled things a little back to front here.

One important challenge for us all is learning to filter out better candidates for our time and hearts at the outset. This section contains some of my personal observations.

One of my own rules when using dating apps (and everyone is different) is not to invest too much time chatting with people electronically. Dating profiles are good for first impressions. Early dialogue with a person tells you a lot; enough for you to know whether you would like to meet them.

In terms of after you meet them and deciding on their date-ability: well, we are all looking for different things. Certainly I would say do not continue to be unconsciously driven by your attractions, especially if that hasn’t got you very far in the past.

Reflect on what your past experiences have taught you Click To Tweet

If you want an easier time in dating, you have to have an honest look at what has happened in the past and use the lessons. Become wise to your typical patterns (we all have them). There are books you can read to educate yourself on this area of your life. Also, I would suggest that you read this article on Attachment Theory. 

How to attract your perfect/ideal partner

Provided you have some self-awareness basics under your belt, you are in a decent position to attract a quality partner if that is what you want. If you are simply interested in casual dating, then this section won’t interest you. 

In terms of looking for your ‘perfect match’ or ‘the one’, I would suggest that you stop looking for needles in haystacks. By the time you find the needle, you might have wasted decades of life and not even be the same person anymore. Instead, it is much better to focus on developing your own value, so that you are naturally drawn to a better quality of person. 

Would your perfect date want you now? Click To Tweet

Whilst you are single, use the time to develop a deep understanding of yourself. As a wise divorcee wrote, we have to be clear in our own minds about what we want, before we have a hope of understanding what our ideal mate would want.

Would your perfect mate want you as you are now? What are your weaknesses/unattractive areas? It’s a tough self-inquiry, but it’s worth the exploration. 

Staying above our biochemistry when dating

Provided you know yourself, you will have a clear idea on what to aim to discover about a person in those early few dates. But part of the challenge is doing that alongside some more primal urges.

In my observations, men seem to make a decision about whether they are attracted to a woman pretty much immediately. Women on the other hand, take some more time to decide, but tend to be firmer in how convicted they are. Both behaviour patterns can lead to negative consequences.

To make truly intelligent choices involves staying above our own biochemistry and impatience.

It is just my personal view, but women stand a better chance of pairing up with a quality partner when they delay physical intimacy for as long as possible. This way, they can stay reasonably objective.

Similarly, men who are serious about finding a long term partner do better to keep their self-knowledge and values at the forefront. And to avoid being too heavily influenced by their attractions.

Gosh, this all sounds a bit unrealistic doesn’t it? I think that anything in this ballpark has go to be better than being guided blindly by ‘chemistry’ and similar forms of elusiveness.


Want to know what I think the most important thing is to do, in order to navigate the world of modern dating?

Know your values and don’t be insecure. Also, keep the standards up on your side of the fence.