Dammit, are you certain about this? I progressed the story because it made me feel like I had to, and I thought the fact that those objectives still showed up meant they were still possible.
I think this occurred as a result of the devs trying to reduce what some complained about "grind" which was not a major problem, and story, which is supposed to occur over time. The optional events do not have to be completed, but I usually have several incomplete ones after obtaining more than enough trust and love to progress relationships. I usually hit the "postpone progress" button for a couple of weeks to mop up anything left over before moving to the next season.
Regarding orgasms early in the relationship, clothes are reducing sensation and they won't get naked just like that, so it is basically a make-out session with heavy petting. If you continue petting the same parts for too long, desensitization sets in and they kind of go numb. This is actually normal in real human beings. This is complicated by each person having their own wants and needs concerning where they are touched and for how long. With Rogue on 250/250 love and trust on the second date and Rogue not wanting to take off her underwear or bra, it is still possible to get her to orgasm. Just as in a real situation, you go for the warm-up first with kissing and touching peripheral parts (thighs low, thighs high, buttocks, breasts, kissing). Once she is warmed-up and "horny" switch over to the main course (crotch) and stop anything that looks like it is slowing down or going negative (watch the arousal meter for any slowing down or reversals). It takes a while with clothes still on, but keep at it and eventually you will see small gains (each round of touching does not always result in the bar raising consistently) until she orgasms. It gets much easier after 500/500 love/trust caps.