I’ve just started dating again after a long-term relationship and a break. It’s a bit overwhelming to start again. What are some fun first date ideas? How do I keep the conversation going? Also, is it okay to kiss on a first date and should you have sex on the first date?
Yours, Navigating New Territory
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Hi Navigating New Territory,
Dating can be exciting, nerve-wracking, and, at times, completely exhausting. The way we meet people and go on dates has changed drastically—especially with the rise of dating apps. First dates can be fun and full of potential, but they can also become draining if you’re constantly navigating awkward small talk and mismatched vibes.
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With this in mind, I’ve answered some common first date questions, to help you navigate those first encounters. Let’s dig in.
The case for Date Zero
One of the best ways to ease into dating again is by embracing the idea of a ‘date zero’—a super low-key, short meetup (around 1-1.5 hours) designed to see if you even want to go on a real first date.
This can help remove unnecessary pressure and allow both of you to gauge chemistry without high expectations. It also makes dating feel more manageable and enjoyable, rather than an overwhelming obligation.
From personal experience, there’s nothing worse than committing to a full meal, only to realise five minutes in that you’d rather be anywhere else. A quick coffee, a short walk, or a casual drink can give you just enough time to assess chemistry without a major time (or financial) commitment.
Make your first real date interesting
If you hit it off, plan something fun for the next date. Playfulness and shared experiences help us bond—whether it’s a rooftop bar, a relaxed picnic or something adventurous. Doing something interactive allows connection to develop more naturally than sitting across a dinner table.
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Who should pay on a first date?
There are no hard rules on this—just what feels comfortable for you. Many people feel women should offer to split but that men should ultimately pay.
Personally, if I don’t want to see someone again, I’ll split so I don’t feel obligated or guilty. But if I do want to see them again, I’ll say, ‘I’ll get the next one.’
Keeping it short with a date zero also helps avoid the awkward ‘who pays’ moment.
Should you kiss on a first date?
There’s no right or wrong answer to this. It depends on the moment and how you’re feeling.
Some people love a first-date kiss, believing that it helps them work out if there’s a spark there. Others prefer to wait. If there’s mutual chemistry and the vibe is right, go for it! If not, no pressure, it’s also okay to let someone know that you prefer to wait.
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Should you have sex on a first date?
Again, this is absolutely a personal choice.
There’s no rule that says sleeping together on the first date ruins a potential relationship (or guarantees one). What matters is whether you feel comfortable, confident, and emotionally ready.
If you’re unsure, ask yourself: Would I be happy with this decision even if I never heard from them again? If the answer is yes, go for it. If not, waiting might be the right choice for you.
First date questions that aren’t awkward
Instead of small talk, try questions that create connection without being too intense:
- What’s something you’re passionate about that most people don’t know?
- What’s the best trip you’ve ever taken?
- What’s a small, everyday thing that makes you really happy?
- What’s the last thing that made you laugh out loud?
- Who’s been the biggest influence in your life?
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Great dates are about connection, fun, and playfulness. Ultimately you want to date someone who helps you feel comfortable, safe and good about yourself. Also know that it’s okay to take a break when dating becomes tiring or overwhelming.
