I am trying to create some lines through this gray area. I feel that there are times when being persistent and showing someone you are interested is attractive since to varying degrees people like being shown others find them attractive, and similarly to varying degrees like being pursued in a positive way.

Also since the two individuals will likely have their own very different lives, there is necessity I would think to have persistence in order to create opportunities for the two people to get to know each other better, otherwise they'll just see each other once and may never bump into each other again, despite there being mutual interest.

Of course the challenge can be reading whether the other person is actually enjoying the persistence, playing hard to get or just flat out getting annoyed by it. For example, I know people and I've actually done this myself sometimes, that become so nervous around a person they like that they end up acting in a rejecting way because they are so embarrassed in that moment or overwhelmed by them. Trying to decide whether this means an actual rejection or otherwise throws another spanner in the works. Or sometimes you and the other person find yourselves in an awkward situation via random circumstances (refer to any rom com for an example) which makes approaching this person a second time slightly awkward too and second guess if you're just going to make them remember the awkwardness from before.

How do I decide whether or not to be persistent in pursuing a relation with other people?

  • Hey FrontEnd, welcome to IPS . Usually, we ask questions to include a bit about culture. This could be e.g. a location tag (different countries have different cultures and as such may require different considerations/skills), and perhaps the age/gender of the people you're pursuing might also play a role here? I could imagine there could be difference between teenage high-school drama's or twice-divorced single moms/dads.
    – Tinkeringbell
    Commented Jun 9, 2021 at 10:19
  • 1
    At some point, there's a trade-off between a risk of missing out on an opportunity with an interested person versus a risk of making someone uncomfortable because you are pursuing them when they don't want it. It's not possible to completely avoid either of those situations. Which one do you want to avoid more?
    – Kat
    Commented Jun 9, 2021 at 17:43

2 Answers 2


In my personal experience there is a clear differences in when persistence is attractive and when it's not. For me there are three situations.

  • Someone is clear on their intentions and I'm interested. They say things like 'Do you want to go on a date?' and I can clearly say that I'm interested. We both know what's going on and if our feeling change, we can cut it off. We don't want to rush into a relationship, but persistence is nice here.

  • Someone is clear on their intention and I'm not interested. This is not a nice situation, but at least I can clearly say that I'm not interested. Here persistence is not attractive. If I tell you no, I mean no. If I become interested, now the ball is in my court and I will approach you to let you know I'm interested.

  • Someone is unclear about their intentions. They seem to flirt with me, but never ask me on a date. They want to hang out, but it's never clear if they mean as friends or as a date. This is annoying. Even when I'm slightly interested, if this takes to long, I will walk away. If I'm not interested and I tell the person, they will act like we were only friends and where did I get the idea they are interested in me? It's annoying. It's an annoying situation for everybody. Like it feels like now I have to get clear about my intentions even though I feel like the person approaching should be doing that. They are probably more clear about their feelings and I'm still feeling it out. I will end up not liking someone, also because they weren't clear about their intentions.

Personally I don't play hard to get and I find the concept outdated. I feel like you can't start a good relationship on those bases. If you're head over heels in love, it can be better to act a bit more cool then you're, but it's never useful to act uninterested when you are interested. If someone does like to play those kind of games, I don't think they are mature enough to have a real relationship with.

In my experience it's always best to be clear on your intentions. If you want a relationship, ask them on a date. If you want a casual relationship, ask them to 'netflix and chill'. Then you don't have to wade through the grey areas, because you both know where you stand and can make future decisions based on that. Grey areas often don't end up going anywhere.

This is completely based on my experience of dating and relationships and what I heard from friends. I feel like I have been in all situations I described. In the first two situations I have been on both sides, on the unclear situation only on the receiving end.

  • I guess the context of the question here would be for the initiator that is quite clear about their intention (hence the need to either be persistent or not), but the recipient is unclear. Your answer gives a good look on the cases where the recipient is clear about their intention. How about the case when the recipient is unclear? (good answer so far, still! Just wanting to add more perspective)
    – justhalf
    Commented Jun 9, 2021 at 9:04
  • Hey josephine! I've edited the question a bit, to make it ask about something that's a bit closer to IPS (how to decide whether or not to be persistent) than having it just ask for opinions on when something is/isn't attractive. I think your answer can mostly stay as is (after all the question still mentions what OP thinks about the attractiveness of pursuit), but perhaps editing the last paragraphs to mention the decision process might be good :)
    – Tinkeringbell
    Commented Jun 9, 2021 at 10:16
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    @Josephine very helpful thank you. I think though the step that is missing is the point from when you realise you are interested in someone to the point where you realise/think they are as well. That whole part is the most gray since you are trying to get to know the other person and gauge whether in fact you are interested enough to go to the next step while at the same time trying to gauge if they feel the same. This is where persistence from the other person can rightly so be considered either welcome or annoying. Once both are confident about going on a date it is less difficult.
    – FrontEnd
    Commented Jun 9, 2021 at 11:49
  • @FrontEnd Well, my advise would be to ask them on a date instead of trying to gauge if someone likes you and if you like them. If the date is a success, you go on the next one, if it's not, you probably don't like each other that much or are not really that compatible.
    – josephine
    Commented Jun 10, 2021 at 7:53

To find an answer, try to look at the problem from a different perspective.

Have you yourself ever been in a situation where somebody you were not interested in tried to get in touch with you, to talk to you, to get a date? You told or showed them clearly that you are not interested at all (and you knew this would not change), but they did not want to hear? How did you feel?

I have been in such a situation more than once, and for me, it is extremely annoying. If I have no feelings for somebody, I certainly do not get them if somebody tortures me with contact attempts and does not accept my "no". On the contrary - such a behavior makes things worse. Who would like to have an obtrusive partner who does not respect other people's wishes and boundaries?

What you can do is: Be patient. If you hear a "no", respect it. If you meet them again, be friendly and sympathetic, but do not talk about meeting again. If the other side is interested, they will tell you sooner or later.

  • I don't think you're taking into consideration the differences between the roles of courtship between men and women and you're also completely missing the point that he is specifically talking about the "gray" area. A definitive "NO" is not gray area.
    – DDSK78
    Commented Jul 27, 2021 at 9:11
  • @sisee very good point, thank you
    – FrontEnd
    Commented Aug 17, 2021 at 11:37

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