10 of my tips for actual dates, as opposed to initial pickup. Source: me, from going on loads of dates in London over the last six years. I’m 29 years old, and generally confident, but I love optimising things so welcome specific insights!

1. When arranging dates, agree to meet her inside the bar / coffee shop / wherever. Never be scared to go in somewhere alone and order a drink while you wait for your date to arrive. Big plus: you get to pick a seat, ideally where you’ll have a great view of the room and she won’t so much. Don't be the loser that waits in the rain outside.
2. It’s cool to choose bars where you can book tables, so you can tell your date to “ask the guy/girl at the entrance where I’m sitting when you arrive”. I like to strike up conversations with the staff at the entrance when I first get there, and I tell them “if you see [amusing description of my date, e.g. ‘bewildered redhead with glasses’] please make sure she finds me, her name’s ___, and I’m __ by the way”. It’s a nice demonstration of social value when the staff member greets your date for you, by name, and mentions you, also by name. Ideally they’ll accompany her to your table, and you can order your date a drink (because you already have one) before the staff member vanishes. Win.
3. Try to get a corner table, so you and your date are not sitting opposite one another, but on two adjacent sides. This is because kino escalation directly across a table is a touch more difficult in my experience than across a corner. You’re also not face-on, which makes you seem less craving of attention.
4. If the bar does interesting gins, wines, cocktails, etc, have one in mind to suggest to your date, because girls will often ask what you recommend. Suggest one that you like, but not the one you’re ordering (unless you’re getting a bottle of wine, obviously). Suggest one that’s gender-neutral (i.e. in the case of cocktails, not a typically girly sweet option, but not an Old Fashioned, either). If she prefers something sweeter, it’s a chance to tease her for having a sweet tooth, and she’ll try to validate herself “I am classy, honest!”
5. Try asking “Have you tried [example of unusual sophisticated thing on the menu, e.g. ‘this Spanish gin flavoured with thyme and rosemary’]?” if she has, great, if not, she might try to get validation by asking if you’ve tried something else she likes. That’s an indicator of interest, she’s trying to compete with your good taste. Good stuff.
6. Choose locations to meet that in an interesting part of town. For example, one of my favourite bars just so happens to be on the same street as a sex shop. If conversation requires it, I can say something like “I swear I saw woman come out of there with her elderly mother when I walked past earlier. Who do you think agreed to go shopping with whom?” It’s always good to tease the subject of sex into conversation. Pay attention and see if perks up at the topic.
7. Avoid classic small talk subjects. “What did you get up to at the weekend?” and “Got any holidays planned this year?” are dire. Even asking what someone does for a living is quite painful. If jobs come up, fine, but don’t bring it up to fill a gap.
8. One of my favourite conversation gap fillers is: “Do you think you can learn a lot about people from…” You can say anything here. Bonus points if it’s situational, for example: “…their cocktail choice”. That’s a fun one for the moment your drinks arrive, especially if she ordered something bizarre. Another fun one is “Do you think you can learn a lot about people from the way they laugh?” I love this. Ask it after a date with a funny laugh laughs loudly. Pause a little after the laugh though… it’s most effective with some dramatic timing. What’s great with these questions is you’re not asking directly about your date, but inviting her into conversations about personality, which girls love. If she makes it about herself, no problem. Just avoid making it about you.
9. It’s often said that changing locations frequently on a date accelerates familiarity by creating the illusory sense that more time has passed. In practice, I’ve often found this unnecessary, but it’s worth a shot if you have some places in mind. It’s not worth leaving a great spot where everything’s going well though unless you’re sure the next place is equally good.
10. Girls are more willing to meet on Friday and Saturday nights if they’re open to the idea of sleeping with you. Remember that. If a girl suggests a date on a Friday or Saturday, take it as big indicator that she’s really into you. Late on a Friday night, after you’ve had a lovely banter-filled, touchy-feely evening, it’s easier than you think just to say, “Let’s get the next drinks in at mine.” On a few occasions, I’ve had girls accept this offer before we’ve even kissed.

PS. I talk a lot about drinking here, it's a common context for dates, particularly in London. But don't get drunk. It won't help. Don't get her drunk either. A little merry is fine though.