Well done, and welcome!
I was in a similar situation to you when I was considering starting at the end of July. I had a holiday booked with a friend in August, and I knew that as we were staying in a self-catering cottage, we'd want to go out for meals at least twice in the week, and from a social POV (and as it was a holiday anyway!) I knew that I definitely wouldn't want to give that up. I had to make the decision: would I start LT before the holiday and still have 2 meals out; would I start LT and somehow not go out for them or go out and not eat; or would I start LT after the holiday?
Well, I decided to start on the 31st July, and in my first 2 weeks I lost 15.6lbs. On 13th August I went on holiday, armed with my LT shakes and more importantly, a plan! I decided in advance that a Sunday carvery would be a good option because I would stick to 'white and green' (chicken / turkey and veg) and stay in ketosis. I didn't have anything to drink except sparkling water, and didn't have a starter or dessert. Later in the week we went out again and I did the same think - meat and veg, no extras, no potatoes etc. Finally, the evening I got home from holiday (20th Aug) I went out for dinner with my OH's family to celebrate a 21st birthday - it was a set meal, but I contacted the venue in advance and said I didn't want starter or dessert, and instead of chicken in white wine sauce I asked for no sauce and extra veg. It wasn't a problem, I still really enjoyed the meal and stayed in ketosis. I confess I did have 1 blip on holiday when I bought a chip-shop fish, but picked off most of the batter and didn't buy any chips. I did have a poor loss that week (0.6lbs) BUT it was still a loss, I had eaten 4 times in a week, and I had a big loss the following week (6.6lbs) which balanced it out.
I think the biggest challenge of having a special meal on this diet is a/ making a plan to enable you to stay in ketosis and sticking to it, and b/ making sure you are strong enough to return to TFR straight after the meal, no questions asked - not letting the meal get you back into bad habits. I KNEW I was going to eat that week, and I KNEW I was back on TFR the next week. I haven't eaten since Sat 21st August, ie when I returned from hols. I have 1 more meal planned between now and finishing TFR, and I know I'll choose carefully, stay in ketosis, and return to TFR until my finish date.