The first time I prayed out loud in a prayer meeting situation I was petrified. I had only been a Christian a few weeks and my new found prayer partners (two nice guys from Sixth Form College, so I was pretty motivated) issued an invitation for me to join in - just trust God and open your mouth - whatever you say will be okay. I can't remember what I did say but during a brief silence when neither of them seemed to be saying anything, I plunged in, the ice was broken and I never looked back.
The whole 'how do I know when it's my turn?' thing bothers some people who are not used to praying extempore in a group; what will happen if two people decide to say their prayer at the same time? Won't it be embarrassing? Generally it's quite amusing and a good test of who is the most humble, because someone will usually stop and let the other person go ahead. If they both stop to do this, you have a problem. But not one that can't be sorted by a bit of good natured, prayerful giggling.
People tend to shuffle a bit just after the leader has signalled it's time to turn general chit chat into actual prayer. (If you're not careful initial chit chat takes up the whole time and no one does any praying). Having liturgy helps here because you have a proper starting point: 'O Lord, open our lips...' It makes a lot of sense.
Adrian Plass used to say that praying people always suddenly assumed 'the shampoo position', though I've never really got this - presumably he meant that when it's time to pray people unaccountably lean forward and place their hands to their heads, but that's not normally how I wash my hair, unless the shower's broken. Furthermore in the hairdressers you lean back into the shampoo position, and I've only known one person who regularly and dramatically did that in prayer, accompanied by a look of anguish, and at the time I used to think 'how can she be so holy?' Now, I think I would assume she'd cricked her neck.
For reasons obvious from the title of these Lenten posts, I found my first experience of silent prayer in a group a puzzling experience. Similarly the habit of some Anglicans to start a prayer: 'Let us pray for....' and then name a person...and then say 'Amen'. I was so caught out by this apparent failure to spell out to the Almighty the details of the precise need (surely He needs a bit of guidance?), then I just got used to it. It's called Churchmanship.
I never could get used to the idea at College that some Anglicans had genuinely never prayed an extempore prayer out loud in a group before, but then those brothers/sisters could not understand my inability to get excited about chanting three consecutive lengthy psalms at 8 o'clock Morning Prayer. I still feel sad that I never heard what came out of their heart in a made up prayer of the moment. But I appreciated their brooding silences after a while.
Silent prayer in a group, I now know, can be very powerful, if all are attending to the Spirit simultaneously. It can also mean that all have fallen asleep, which is not so good. A lot of Google images for prayer have groups of people holding hands whilst praying. I love this idea in theory...
So however you're praying this Lent, out loud, extempore, in a silent group or a liturgical group, for the first time or for the umpteenth, remember prayer is always for beginners.