Ask at the end of the first date, in person, while the night is still good. Name a specific day and a specific kind of place, say it once, and take either answer calmly. Asking does not sound desperate. Vague lines, repeated questions and a fallen face do. A man who says "I'd like to see you again, are you free Saturday afternoon?" sounds confident, because he knows what he wants and can live with her answer. If you ask by text the same rule holds: one clear message beats three, and a woman who likes you will answer it.
What desperate really means
Desperate is not the act of asking. It is the sound of needing the answer. Three habits create it.
Vagueness. "We should do this again sometime" forces her to do the work of making the plan or to say no for you. A vague line is also easy to say yes to and never follow up on, which leaves you checking your phone.
Repetition. Asking twice in the same hour, or following a no with "are you sure?", tells her your comfort depends on her.
Visible disappointment. If she needs to check her schedule and your face falls, she feels responsible for your mood.
Remove those three and you are left with a man making a clear, friendly request.
When to ask
Ask before you part, while the date is warm. A common mistake is to say goodnight, go home and then wonder for two days whether to text. Asking in person is easier to read and easier to say yes to, because she is in a good mood and your voice and face are right there.
Choose a moment near the end, when the energy is still high. Do not ask in the middle of dinner, and do not wait until the awkward curb where you are both unsure how to leave. If you are walking her out, say it before the hug.
If you forgot or lost your nerve, text the next day. That is the second best time. The earlier, the better.
What to say
Short, specific and tied to something from the date.
- "I had a great time tonight. I'd like to see you again. Are you free Saturday afternoon?"
- "You mentioned you've been meaning to see the new gallery downtown. Want to go Thursday after work?"
- "I'm glad we did this. There's a place near me I think you'd like. Are you free this weekend?"
Name the day, and a time of day if you can. Pick a day a few days out, which gives her room to fit you in.
Tying the plan to something she mentioned shows that you listened, and it gives her a reason to say yes. It is easier to agree to the gallery she wanted to see than to a vague evening.
What to do with each answer
She says yes. Good. Confirm the day and say you will text. Leave it there.
She says "let me check." Say "Sure, text me when you know," and mean it. Do not fill the silence with another plan. Let her answer in her own time. A woman who wants to see you will usually reply within a day or two.
She names a different day. That is a yes. Take it.
She says "maybe" or something vague. Smile, say "no problem," and leave it. A "maybe" with no day is usually a gentle no. Do not chase it.
She says no. Say "Thanks for coming out, I enjoyed it," and mean it. If you respond with grace, she remembers it as a good evening. Then move on.
If you texted instead
Keep the text short and concrete, and send it the next day.
- "I had a great time last night. Want to try that bakery you mentioned on Saturday?"
Do not write a paragraph about how much you enjoyed it. Do not send three texts in a row. Send one, then do something else with your day. a dating coach says the best thing to do with texting before a date is to keep your messages few and leave a reason in reserve for later. Wait for her reply before sending anything more.
If she has not answered after two days, you can send one light follow-up. After that, stop.
Plan for the second date during the first
coach has a useful point about logistics. On a first date, pick a place near your own, so that if it goes very well you have easy options, and if it goes just fine you can leave without trouble. He warns that a great date can end up going nowhere simply because it was too far away. If you plan so that a second date is easy, you will not need a clever line to get one.
Also, have an idea for the second date before you ask, so you can say it right away. A man with a specific idea sounds sure of himself.
What not to do
- Do not ask whether she had a good time more than once. It sounds like fishing.
- Do not send a long text of feelings.
- Do not ask her friends to find out.
- Do not post about her.
- Do not apologize for asking.
- Do not take a "maybe" as a promise.
The simple version
Ask in person before you part. Say the day and the kind of place. Say it once. Take the answer well. A man who does that is not desperate, because he has shown he does not need a particular answer to feel okay.
Written by Matthew Stevens, Co-Founder & Head Coach. More than half a decade coaching men across the US and worldwide.
Everything here comes out of real coaching work: the approaches, dates, texts and profiles we go through with the men we coach.




















