After a second date, send a warm, specific message if you enjoyed it, mention something you genuinely shared, and be clear if you'd like to see her again. “I had a lovely evening. I'm still laughing about the disastrous cheese tasting. Would you fancy seeing that play next weekend?” is enough. A second date may mean the two of you are getting to know one another better, but it doesn't automatically make you a couple. Don't assume exclusivity, demand instant replies or invent a timetable for the third date.
My friend Aloysius has always had a fondness for ceremony.
After an enjoyable first date with a woman called Rosamund, he sent a tasteful thank-you message and arranged to see her again.
The second date was a cheese-tasting evening in the back room of an independent food shop.
By all accounts it was a triumph, apart from one small incident involving a particularly adventurous blue cheese, a silver tasting fork and a piece of bread that departed from the table at considerable speed.
Aloysius was delighted. So delighted, in fact, that he began composing a letter announcing the beginning of their “romantic partnership”.
“Have you asked Rosamund whether she wants to become your romantic partner?” I enquired.
“Well, we've had two dates.”
“And have you become engaged?”
“Of course not.”
“Splendid. Then perhaps don't announce the founding of a new royal dynasty. Try telling her you enjoyed the cheese.”
At the end of a second date, you may have a stronger idea of whether you enjoy somebody. Your next message can reflect that growing familiarity without claiming more than the two of you have actually agreed.
The first question is whether you'd like a third date
Before deciding what to write, consider what you want.
Did the second date feel enjoyable? Did you discover something new about her? Did the two of you find conversation easier than the first time? Would you genuinely look forward to another meeting?
You don't need fireworks or a dramatic declaration. Curiosity, warmth and attraction may be quite enough.
But don't send a romantic promise simply because a second date seems to require one.
If you didn't feel the connection develop and don't want to meet again, you can be honest and kind.
If you're uncertain but would like to know her better, you may choose another meeting without pretending you've made a lifelong decision.
The point is to respond to the actual woman and the actual evening, not a set of imaginary rules about what the second date must mean.
A good message refers to something the two of you shared
After a second date, you usually know a little more about her than you did after the first.
Use it.
“Last night was lovely. I haven't laughed so much at a museum since the guide accidentally locked himself in the model railway room.”
Or: “I'm still thinking about your story of the terrible school play. I had a brilliant afternoon.”
Or, if the mood was quieter: “I really enjoyed our walk and the conversation afterwards. It was lovely getting to know you better.”
These aren't extraordinary literary achievements. They show attention.
Avoid the generic line that could have been sent to anybody you've ever met.
And don't force humour where it wasn't part of the evening.
If you both had a thoughtful conversation about family, a simple sincere message may be more appropriate than a spectacular joke involving penguins.
When should you send it?
You don't need a secret twenty-four-hour strategy.
If you've just said goodbye and would like to thank her later that evening, do so.
If the date ended late, a message the next morning may be perfectly natural.
There's no universal countdown clock that determines whether genuine interest will survive.
UK dating advice from eharmony recommends a relatively prompt, personal note after a second date if you'd like to continue seeing each other.
But the person you're speaking to may have a different schedule or communication style.
Don't insist she reply immediately, and don't punish her for sleeping, working or travelling.
The useful thing is being clear that you enjoyed the experience, not winning a race to hit Send at the theoretically perfect moment.
Aloysius and the runaway bread
The cheese-tasting disaster was not entirely Aloysius's fault.
A shop assistant had presented an especially pungent blue cheese.
Aloysius, who believed himself a man of refined taste, announced that he could detect “notes of woodland, rain and noble decay”.
Rosamund examined her own portion.
“I can detect a very determined smell.”
He attempted to demonstrate the correct way to handle a small silver tasting fork.
The fork slipped. A piece of bread flew across the table and landed in a decorative arrangement of artificial grapes.
Everyone stared.
“An expressive finish,” Rosamund observed.
Aloysius bowed his head.
“I fear the cheese has defeated me.”
She laughed so hard that she had to put down her glass.
That was the evening's private joke. It belonged to the two of them, and it offered an obvious subject for a warm message afterwards.
Instead of announcing a new relationship, Aloysius eventually wrote: I've had a wonderful time. I fear the blue cheese will haunt me, but your company was absolutely worth it.
Rosamund replied with a photograph of the offending cheese and the caption: Your oldest enemy.
How to say you'd like to see her again
If the evening went well, you can be clear about wanting another date.
“I've enjoyed these two evenings with you. Would you fancy going to that little comedy show next weekend?”
Or: “I loved tonight. I'd really like to see you again when you're free.”
A second date often gives you a better idea of shared interests, so draw on those.
If she mentioned a play, concert or place you'd both enjoy, you have a natural idea for a third outing.
But don't purchase costly tickets without agreeing on the plan, and don't assume she has the same free time you do.
An invitation remains a question, even after two dates.
She is free to say yes, ask for more time or decide that the connection isn't for her.
Don't assume two dates mean exclusivity
One of the most spectacularly avoidable mistakes is treating a second meeting as an unspoken contract.
Perhaps you feel very attracted to her.
Perhaps she likes you too.
That does not establish that either of you has agreed to stop seeing other people.
Different people approach early dating differently. If exclusivity becomes important to you, discuss it at a suitable time rather than assuming the answer from a pleasant evening.
Don't send “Now that we're official…” unless you have actually spoken about being official.
And please don't introduce her as your girlfriend to a room full of friends without asking.
Aloysius had already considered commissioning two engraved napkin rings.
I suggested he might first establish whether Rosamund wanted another evening in his company.
A genuine relationship is something you build and agree on together, not something one person can declare into existence.
What if the second date was more romantic than the first?
Perhaps there was a kiss.
Perhaps you held hands or felt more comfortable flirting.
You can acknowledge that with warmth if the exchange was genuinely mutual.
“I had a lovely evening with you. I've been smiling about our goodbye.”
You don't have to turn it into a detailed discussion of physical intimacy by text.
A kiss doesn't promise further affection on the next date, and two dates don't establish permanent permission for anything.
Let your messages reflect the connection without making her uncomfortable.
If you're not sure how romantic she'd like the conversation to be, stay gentle rather than escalating with explicit remarks.
Two adults can enjoy attraction while continuing to discover each other's boundaries and preferences.
What if she sends the first message?
Wonderful. Read what she's actually said and answer it.
If she writes “I had such a good time,” you might reply, “So did I. You're remarkably good company, even with that cheese's best efforts.”
If she suggests meeting again, you can help arrange it.
There's no law requiring a gentleman to make the first move after every date.
Don't wait deliberately because a theory says the person who responds last has romantic power.
If you enjoyed seeing her, show that naturally.
And if you need time to think, you're allowed to say so. Courtesy needn't involve instant access to your phone.
The aim is a pleasant exchange between two people, not a battle for control of the conversation.
What if her response is polite but cool?
A second date doesn't always create a spark for both people.
Perhaps you send a warm message and she replies briefly without showing much interest in another meeting.
Don't conclude that she despises you, but don't ignore the possibility that she's uncertain.
You can make one straightforward invitation when it feels appropriate.
If she declines or consistently avoids any further plan, let the matter rest.
Repeated persuasion won't create attraction, and accusing her of “leading you on” because she accepted a second date is unfair.
People are allowed to explore whether a relationship might work, then decide it doesn't.
You can be disappointed without transforming the ending into a personal feud.
Good manners become particularly valuable when two people want different things.
How to keep chatting before a third date
Once the two of you agree that you'd like to meet again, there's room for ordinary conversation.
You might send something that reminded you of a shared joke, ask about an event she was looking forward to or follow up on a subject you both enjoyed.
But don't set a daily message quota.
Some people like frequent small updates. Others prefer an occasional note or telephone call.
If you notice that your rhythms differ significantly, discuss it rather than guessing what she means by every delay.
You shouldn't have to spend the week performing elaborate charm exercises to prevent the relationship disappearing.
There is a life beyond the telephone, and an early romantic connection should leave room for both people's ordinary responsibilities.
If you don't want another date
Perhaps you enjoyed her company but aren't feeling the romantic connection you hoped for.
You can thank her and be honest rather than promising a third meeting.
“I've really appreciated getting to know you, but I don't feel we're the right romantic match. I wish you all the best.”
Use language that sounds like you, without unnecessary criticism of her appearance or personality.
You don't owe someone a long list of reasons. You do owe basic courtesy when you've been dating and communicating.
A short clear message can be kinder than disappearing after two evenings together.
And if she says she doesn't want to continue, accept that with the same grace.
Not every second date is a prelude to a third. Sometimes it simply tells two people more about whether they suit each other.
Rosamund's invitation to the third outing
Aloysius resisted the temptation to order engraved napkin rings.
Instead, after their cheese-related messages, he asked whether Rosamund would like to visit a small theatre together the following week.
She agreed.
On the night, she produced a tiny novelty cheese fork from her handbag and handed it to him before the performance.
“For luck,” she said.
He laughed, put it safely in his pocket and promised not to launch anything during the interval.
Their connection was developing, but no titles had been conferred and no ceremonial decrees were required.
They were still two people deciding whether they wanted to spend more time together. That was quite enough.
After a second date, send a message that shows you noticed and enjoyed the person, then be open about what you'd like next without claiming that anything has already been decided.
If my method of wooing appeals to you, the little free fourteen-page booklet can be claimed from this page's invitation.
And Aloysius, for pity's sake, keep the cheese fork away from the upholstery.