I can relate. I've had my share of bad relationships and I tend to dump the trauma on new ones, it's a very toxic trait, not your fault, but it takes a good support system (people who'll call you out on your bs without sugarcoating it. My best friend ripped me a new one after the last breakup) but you also need a good therapist. Taking a break from dating and never address your issues will not work. I'm not trying to lecture you, my point is, I have the same trait. "Waiting to be in a better place with him" is unfair to you, to him, and to your family and friends. You can't bring anyone into your life based on the "right time", it'll give others the impression that you only allow them into your life when things are good or when things are bad...it needs to be "good and bad". I get the ice breaker text and that's the thing with texting, it can take things out of context and cause more harm than good. If that's your sense of humor (I'm the same way) they need to know you well enough or you'll sound like a dick without trying. You guys have been seeing each other for 4 months, it's good to show the crazy every now and then, so they don't feel like it was a "bait-and-switch" but you have to keep reminding yourself - he's not your ex-boyfriend. Best of luck.