Let’s break down the real timeline and events of this relationship, in your own words:
At date 4: “we fooled around some but didn’t have sex – he actually admitted he is inexperienced compared to me and clearly felt nervous about it.”
You instigated intimacy, which made him uncomfortable, which he reveals a bit to you then, and later very clearly. He tells you that he is a virgin.
After date 5: he cancelled. “So today was meant to be our sixth date….The truth is I am feeling quite vulnerable as this is the first person I really opened up to after my last break up and I think being naked together last time has exacerbated things. Am I reading into things too much and should contact him again to confirm the date tomorrow?”
5 dates in, less than 5 weeks, and you are panicking because he cancelled a date suddenly. When he says he is sick, you immediately follow up with, “Ok, how about TOMORROW” which isn’t a realistic recovery period to someone who is actually ill. You were pressing for him to see you again, as soon as possible, because it provoked insecurity in you. Except that you also know that he is a virgin, and that intimacy at the level you instigated made him uncomfortable, because he has told you this AND started trying to have “in public only” dates with you.
Then, you say this in response to someone suggesting you let him make the next plans and pursue other potential TRULY available men: “I guess I can, but I feel I’m working pretty hard here. He should have reached out to cancel/reschedule. I then both made the reservation on phone and had to change it again.”
You are guiding and forcing the relationship already, at date 5. In fact, you say after your first “taste” of intimacy with him that you want to keep GOING INTO PRIVATE PLACES LIKE HOMES, and not make out in public, because he is clearly trying to keep you in public places. And you don’t like that he has set that boundary.
Date six HAPPENS, and he is indeed sick! You say: “So he does look a little sick/pale & he tells me he was not going to blow me off, but was waiting another hour in the hopes he would feel better. Sounds plausible. However, he mentions that he doesn’t feel ready to be in a relationship and would prefer something more casual right now.”
He tells you that he does not want a serious relationship with you. At date 6. He goes on to say that he does not want a physically intimate relationship to the level you want. You now know that he is a virgin, is uncomfortable with sex, and is reacting by pulling back. He asks to take things very, very slowly. But this is what you say:
“The bad: He has outright said he wants casual/not a relationship and I don’t think there’s 100% clarity on what that means yet. Like, does it mean he is just going to contact me/arrange dates whenever he fancies it? Because if so that puts him in the driving seat & where does that leave me?”
Your friend says, “a friend also suggested that because he said he doesn’t feel equipped to have a relationship right now, he might have no intention of sleeping with me at all or coming home with me again etc. Hence why he is intimate in public, but not asking me back etc”
You mention understanding, and say you’ll take things slow and respect his feelings. Great, you are going to respect his boundaries and not force intimacy yet! But, wait…no you aren’t, because then somewhere between date 6 and date 10 while you pretend you are ok with that, this happens:
“For a new relationship things have intensified quite quickly. On the last date he intiated things sexually, but at one point he stopped me and told me that he was abused as a child doing this particular act Clearly it triggered him, and we talked. I asked if he wanted to stop the sexual part of the relationship for a while? He said no, he’s happy to continue, just not doing this particular thing.”
And again, predictably, because you are pushing his boundaries, he pulls back away from you. This is how you respond:
“It makes me feel he is NOT into me, which is bizarre given how INTO me has been behaving.” “…It’s blatantly clear that he is purposefully not contacting me.”
So you need him to disregard his own boundaries and feelings because you kept provoking intimacy and then it made you feel exposed. Mind you, this is a (now former?) virgin with sexual assault as his childhood background.
Predictably, your relationship (likely) sends him into a deep depression while he tries to work out what he went through in the past, how to handle his relationship with you, and process his physical and emotional feelings. This is two months in, right when you are starting to insist that he needs to text you regularly (more regularly than your ex, who texted every 3 days and then you “had to talk to him about it,”) and that you wanted to discuss sexual exclusivity with him. Seeing that he was a 23 year old virgin, I don’t think him cheating on you physically was the problem. Instead, you felt rejected right when you were feeling most vulnerable. And you want his fulltime reassurance, attention, and continued physical affection to reassure you.
This eventually leads to you breaking up with him after a romantic night, possibly because you were trying to press him to give you something he couldn’t in commitment and communication amounts he was not able to provide while working through his issues. And then, when he doesn’t fight you on the break up, you are shocked and sad and want to find a way to keep dating…or…be his “friend.”
And now, just 3 months later of playing politely in the friend zone, you think you can make it work again. By, what else? Taking the lead (again) and pushing him to ask if he wants to try again. Here is one of the sympathetic to his turmoil things you said:
“– We have already been intimate, so I’ve had a taste of it and I suppose crave it more”
Stop pursing and forcing a relationship that isn’t working. Every step of this journey he has been honest with you about what he can handle, what he can’t, what he wants and what he needs from you. Every step of the way, your own insecurity and needs push his out of the way and demand something of him and push him into the discomfort zone that has put you in the “not quite friend” zone that you want to change. It drove you crazy with insecurity, it literally helped spark a bout of depression in him.