How to know when to stop chasing
Dating does require a certain amount of courage, whether that means sending the first message, suggesting another date or allowing a connection more time than you initially thought you would. The difficulty is knowing when healthy effort has started to become chasing, because when you genuinely like someone, persistence can feel very similar to optimism. The more useful question is not whether you should try harder, but whether the relationship is beginning to develop through mutual interest or whether you are the person creating most of the momentum.
Have you fallen for the person, or the future you have imagined?
This is particularly relevant to what we call the Dreamer in our dating personality quiz, because Dreamers are often very good at seeing what something could become. They meet someone they are excited about and quickly begin imagining the trips they might take together, the people they could introduce them to, the weekends they might spend together and the kind of life they could eventually build.
There is something lovely about approaching dating with that level of hope, and as we were discussing as a team recently, you could just as easily call some of it manifesting. Believing that a great relationship is possible can help you stay optimistic and receptive, but the challenge comes when the imagined version of the relationship begins moving faster than the real one.
When that happens, it can become difficult to separate your feelings for the person in front of you from your attachment to everything you have pictured happening next. Walking away can then feel much bigger than ending a handful of dates, because you are also letting go of a future you had already begun creating in your mind.
A useful question to ask yourself is: Am I disappointed by what is actually happening between us, or am I disappointed by losing what I hoped this could become?
Instead of counting texts, notice what happens when you reach towards them
The Gottman Institute talks about “bids for connection”, which are the small attempts we make to gain another person’s attention, affection or engagement. Their work looks at whether someone tends to turn towards those moments of connection or move away from them, which provides a useful lens for early dating because interest is usually revealed through a pattern of small responses rather than one dramatic gesture.
You suggest meeting again and they help make the plan happen. You share something about your day and they become curious. Plans change and, rather than leaving things hanging, they offer another time. These moments can tell you much more than whether somebody took two hours or eight hours to reply to a message.
A delayed text can mean very little on its own, whereas a repeated lack of engagement tells you far more. The learning here is to pay attention to the overall pattern rather than becoming fixated on isolated moments, because if you are repeatedly creating opportunities for closeness and the other person rarely meets you there, you may already have the information you are looking for.
Instead of asking yourself whether you should send another message, it can be more revealing to ask: When I reach towards this person, do they generally reach back?
What does it feel like to be the person being chased?
Last week we talked about being open to opportunities, allowing connection time to develop and not dismissing someone before you have really had the chance to know them. That still matters, but openness should not require one person to carry all the emotional momentum while the other simply goes along with it.
Being pursued can feel wonderful when the interest is mutual, but when one person is much further ahead emotionally, that attention can start to feel more like pressure. You may find yourself replying because you do not want to hurt their feelings, accepting another date because saying no feels uncomfortable or continuing a connection because you know the other person is excited, even though your own feelings have not developed in the same way.
That does not necessarily mean anybody has behaved badly; sometimes two people are simply moving at different speeds. However, it is worth asking yourself whether you are giving someone genuine encouragement because you want to keep exploring the connection, or whether you are participating because disappointing them feels difficult.
Clarity is often kinder than creating momentum you do not genuinely feel, just as stepping back can be healthier than continuing to pursue someone who is not meeting you in the same place. The strongest relationships leave room for both people to move towards each other by choice, rather than one person persuading and the other trying not to disappoint.
After all, as the saying goes “if someone likes you, you’ll know, and if they don’t, you’ll be confused.”
A few things to take away
Be mindful of becoming more attached to the future you have imagined than to the connection you are actually experiencing.
Manifest the kind of relationship you want, while still allowing the person in front of you to show whether they belong in that picture.
Look for patterns of engagement rather than overanalysing individual messages, dates or moments.
If you are doing most of the pursuing, create enough space to see whether the other person moves towards you without prompting.
If you are the person being pursued, make sure your responses are coming from genuine curiosity rather than guilt or obligation.
Wondering if matchmaking could work for you? Book a call with our team to learn more.