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?
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.0