The trick is not minding that it hurts.
Now, obviously, if you can accomplish your goals without getting any scrapes and bruises, that's better. It's just not always possible, especially when learning something new and this goes double if you are, in some sense, breaking ground.
Smooth seas do not make skillful sailors.If you are LGBTQ and coming out of the closet, you are breaking ground, if only for you. You may be able to learn from the experiences of others and this may help you hurt less, but to some extent your experience of coming out will be unique to you, your life and your circumstances and there won't be a perfect match you can simply copy.
-- African proverb
Because I was sexually abused as a child, I spent a lot of my life trying to sort out my sexuality even though I mostly wasn't sorting out questions of my orientation. I kissed a few girls from age 11 to age 16, then began menstruating and suddenly was all about the boys and never looked back.
But I had a lot of other questions about myself and my sexuality and my life and I had trouble even asking them, much less answering them. This was true in part because I got married at age 19, so my sexuality was not simply "mine."
For a lot of years, my sexuality was part of this longstanding relationship and I didn't know how to separate some details until I was getting divorced and that stopped being true. So during my divorce, I made the conscious decision that "Mistakes will be made" and I decided to just suck up a certain amount of pain and then shake it off.
I made sure to limit how much downside there was so that accepting some pain and suffering wasn't ruinous to either me or other people, but I did just go "Oh, well, this is going to hurt sometimes and I am going to do it anyway."
My life was really screwed up in a "It is literally KILLING ME" kind of way. I decided I was going to fix my crap or die trying, so I sometimes found myself in some pretty emotionally uncomfortable situations.
Pro tip: IF you take a similar approach, be prepared to ditch a few people.
If you agree to do X with someone new, it's probably something they've done before and agreeing to it once tends to set a precedent such that they will expect more of the same. If you don't want to keep doing it and telling them "I don't want to do that anymore" isn't getting results, the only real solution is to dump them.
The reason for this is because if you tell them X thing is unacceptable and they keep doing it though they've been asked repeatedly to stop, it tends to turn into an abusive relationship where NOTHING you say matters. They will just willy nilly do as they please and not care what you say and it will get worse and worse over time.
So it is my personal policy that if I have to ask a new person repeatedly "Please don't do X," then I ditch them and don't look back, no matter how much I otherwise liked them.
If you are really vulnerable, you may need to just stop the dating game for a while, deal with you and get back in the game at a later time when you are less vulnerable. This is a factor in why I have been celibate for more than sixteen years.
I usually describe that as "I have been celibate for medical reasons for a long time" but it's not that simple.
During my divorce, I was newly diagnosed with a genetic disorder and I had some kind of antibiotic-resistant infection that doctors were failing to identify and I was cycling through a lot of antibiotics. After the third guy in a row failed to follow instructions and supply a condom for medical reasons and I stupidly got jiggy with him anyway, I decided: I'm too sick to play this game.
Once is an accident. Twice is a coincidence. Three times is a pattern.So I decided that I am just not going to play this game until I am physically healthy enough to not be so worried about the medical stuff and also in a better place where I feel I can say No glove, no love, put my clothes back on and LEAVE if necessary.
I'm a conflict avoider and prefer to just walk away from drama if at all possible. While sick and going through a divorce and so forth, I was just not in a place where I could stand up for myself and I decided this was not acceptable.
It was a danger to my health and to the health of other people -- people who were failing to grasp that my unidentified antibiotic-resistant infection was a danger to them, even though my genetic disorder per se was not -- and I needed to just stop it.
Having learned from experience that men were not listening and I was failing to do what was necessary when push came to shove, I decided to simply stop for the time being. I haven't as yet found a situation where it made sense to me to get back in the game and I don't know what that would look like. Hopefully, I will know it when I see it, as they say.
I have no desire to enumerate the myriad ways some men were genuinely shitty to me during my divorce. I did what I could to limit the downside and I decided just how much crap I was willing to put up with and when I hit my limit, I noped out of both individual situations and ultimately of the dating game entirely and I also consciously decided to just not carry a grudge or whatever.
Mistakes were made. In the aggregate, I got what I needed out of it. I just don't bother to dwell on some of the crap some of these people did.
I operated on a No harm, no foul basis and did my best to make sure no one was in a position to do real harm. Any relatively minor pain and suffering that were part of the process, welp, I licked my wounds and got the fuck over it.
Because I decided that's just how that will go if I am ever going to sort my personal crap and not sorting my personal crap would hurt more than sorting it. So: Whatevs.