When to have the chat?

[tiptonguepheno]

We have been dating for 2 months, both in our early/mid 30s. I initially told him I wanted something casual as I was very occupied recovering from knee surgery and having physio, but this has now eased.

Prior to telling him I wanted something casual, we went on some very nice dates. Since telling him I wanted casual, we have mainly met for sex twice a week. He has occasionally invited me to do other fairly relaxed things (sunbathe, coffee, look at areas he wants to move to), but I have had to decline as they have been last minute and I am busy.

I want to change the nature of our relationship from casual to serious, but worried that it may be too late now. I want to talk to him about it, but want to get my words straight and need a little help with that.

I am enjoying his company and would feel a lot more comfortable if we were in a secure relationship, for a variety of reasons. We have been tested and he is suggesting we figure out contraception so we can go condomless. I am not comfortable not using condoms if not in a secure relationship.

How do I best approach this?

I would just sit him down in person (definitely not text, there’s too much to hide behind) and say you’re at a place in your life where you’d like a serious, committed relationship and that you’d like that to be with him.

I see it as a good sign you seem to be exclusive anyway. I assume so if he's not wanting to use condoms and he invites you do things other than sex.
I would say what you explained here, you only want to as part of a committed relationship, and hear what he has to say about that.

Make it obvious you want something serious then he will be the one to tie you down. If he doesn't, then that will be because he doesn't want to.

Just talk about it casually that you realise you want a serious relationship, a family, children etc. and you need to find the right person for that.

If he thinks it's him he will do something, if he doesn't you have your answer.

Men don't wait around for things like this.

@latriciamcneal why such elaborate game playing? This can become a comedy of errors with misunderstandings

@tiptonguepheno just tell him what you have written here.

What worries you about telling him? I mean, people say things clumsily all the time, and that's fine. What do you fear could go wrong?

Just ask him, he will either say yes or no.

Just say that you know you told him that you wanted something casual, but actually you've now realised that you want something more with him, how does he feel about that,

Just do it, you're over thinking it.

Just casually chat about it. Say something like ‘I know I said a few weeks ago I was only interested in a casual relationship, but I now feel a bit different and would like us to progress a bit further’. ‘How do you feel about things yourself?’
Keep to light and easy.

Cross posted with LoveSpringDaffs!

Just tell him now you've got your knee op and recovery out of the way you've got the capacity for a more serious relationship and want to make clear you'd like that with him, if he feels the same.