I want to make the first move, but need some tips. Please help miss clueless here?

I had a relationship that ended 5 years ago due to being on different pages in life. The relationship itself was light, fun and we never had an argument.
He moved overseas i was going to come for part of it but it didn't work and i think he wanted to do it on his own being only 21 at the time.
At the time i think i was getting over someone else still so i didn't completely invest in the relationship and found him too immature to have a future with.

1.5 year later he returned we caught up one night had sex and he attempted to catch up but i was shy and he hadn't changed so i backed off.

1 year later we tried again, he did not want to have sex though as he "wanted to make a good impression". He said he was shy, hurt that i never said i loved him and that he wasn't close to my family. He said we should work on things and that was it.
I could have made a move but as he broke up with me i felt i need him to do the putting back together.

2 years later (present). I've finished university moved out of home and am looking for jobs in my field. He is different too; he doesn't enjoy partying as much, he bought a house, and he now owns a 1/3 of the business he works for.

I spent a rather nice night with him, both of us were quite nervous and shy. He stayed over and we had sex, and he wanted to cuddle all night. In the morning i could tell he wanted to have a serious conversation but could not get the words out. Eventually he asked " Do you want to catch up again". In my head i was screaming YES, but it came out as a casual yes.

I can see that this has the potential to go as before, i. e. nothing eventuates. However this time we are both different.
I am thinking that i should ask him to catch up this week so he knows i am definitely interested however I don't know how to go about it what to say and when to do it, or if he was even serious.
He stayed at mine on Friday and it is now Saturday night, is it too early or late or should i wait and see if he asks first?


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Most Helpful Girl

  • There is nothing wrong with making the first move. But this time, avoid inviting him to yours or you to his. Because while you are in a private set up, you will eventually get carried away and have sex without the "catching up part". Best to meet him out for coffee or dinner, depends how familiar you guys are with each other. Meet him out in public so that you guys don't get carried away. Know where he and you stand and see if you are both willing to work on things this time around.

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What Guys Said 3

  • You are asking for trouble once again..

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    • 1mo

      do you think i need to make it more obvious that i am interested? I can be quite a blank canvas as i talk to everyone the same [so i have been told]

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    • 1mo

      the reason i asked as we had a very easy break, and there was no hate on either party. I'm still yet to have a disagreement with him. I have attempted in the past in other relationships to do this but it was a terrible end.
      I see this particular instance as a matter of bad timing in the past. There is a lot that i left out, for example i lived at home until i was 26 as i was studying three degrees at university. They would not let me have my bf's stay or come over so everything was in the relationship had to be one sided.
      I struggle to show my interest in potentials partners as i was burnt badly and as a result i can seem disinterested when its quite the opposite

    • 1mo

      It doesn't matter. There are always going to be situations happening. If you feel this strongly then go for it. I can only give my opinion. I predict it won't work though, not to be negative, just honest.

  • All you need to do, is find a way to talk with him, and connect with him. That is all.

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  • Wish more girls did it

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What Girls Said 4

  • You need to just seriously leave this guy alone. Both of you are unstable and your using each other for sex. Is that what you two define as a relationship? The way how I see it is that your allowing him to string you along. Your attached to the sex, and it sounds like he was also your first sex partner too. Just know that it doesn't sound like he is interested in another relationship. But to be in a relationship where he is just getting sex. Its going to be the same thing all over again. But if that is what you want to do again, then just tell him.

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  • If you do the same things you get the same results.
    If you like him don't wait for him to make the move, given you guys have been back and forth so many times over the years he is interested! So let him know you are too.
    What have you got to lose by playing it so closed?

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    • 1mo

      i agree with you. Its been such a long time since i have dated I'm not sure if i should wait a day or two. Im worried it was a throw away comment.

    • 1mo

      But he might feel the same way - and is worried that because you didn't say YES the way you wanted to you're not all that interested and just agreed to not be rude. If you like him then show it, if you don't then gently let him know and move on.
      Send him a message, say you had a lovely time and you're looking forward to seeing him again if you don't want to push for a date and time

  • I'm not sure if your term "catch up" Where I'm from it means get together and fill each other in on what's been going on in our lives. Talk. It sounds like if your having sex again you're beyond catching up.

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  • He is shy, so you should take initiative without being too agressive. Sooner or later there will be an occasion where he opens his feelings, but its like a heavy door he has to push to open.

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