Keep every text short, make it fun to answer, and aim the whole chat at a specific plan. Texting a woman you want to date is not a way to get to know her forever. It is a way to get you both to the first date. If you are also wondering whether to ask her what she wants to do, the answer is no. Bring a plan, and offer her a choice between two. The same is true for messages on dating apps.
What the texting is for
coach puts it plainly: texting is not the best way to communicate. Meeting in person is better, and a phone call is next. Texting exists to get you to one of those. You are not going to share your deepest feelings by message, and you are not going to build a relationship in one long string of jokes.
That changes what a good text looks like. It is a short, friendly, slightly playful exchange that ends with both of you knowing when you will see each other. If a chat has run for days and no plan has been mentioned, it has already drifted into pen pal territory.
Show that you are interested, without gushing
A woman wants to know that you like her, and she also wants you to be a man with a life. Both can be true at once.
Be a little direct about your interest. Tease her, compliment something specific she said, and let the tone have some warmth. Skip the paragraphs about how amazing she is. My point about long texts is that they look needy and are tiring to reply to, so one or two ideas per message is the limit.
A good example: "You have the worst taste in restaurants and the best taste in everything else. I am going to need to supervise Thursday." It is warm, a little cheeky, and it mentions a plan.
Start the plan early and in pieces
Do not hold back the invitation until you feel brave. Plant it early with something casual, like "we should test that ramen place you mentioned." Let it sit for a message or two. Then make it specific: "Thursday or Saturday?"
My closing method works well here: qualify, confirm, close. Check how she feels about the idea in general, confirm that you both mean it, and then pick a time. Each small yes makes the next one easier, and you avoid sending a single large invitation that can get a single large no.
Should you ask what she wants to do on a first date?
No. Asking "what do you want to do?" hands her the work of planning your evening, and it makes you look like you do not have a view. coach is clear that you should have a plan for the date.
That does not mean being rigid. Offer two options: "Drinks at the place with the patio, or a walk and a drink near the park?" She can pick without having to invent anything.
coach also prefers drinks to coffee, because the setting is more relaxed and it is easier for the two of you to get closer. He avoids shows and movies for a first date, because you spend the time watching something instead of talking. A first date should leave room for you to actually interact.
It also helps to choose a place near you or near her, so that a good evening has somewhere to go.
Keep the tone informal
When you are making plans, do not let the chat turn into a string of logistics. My advice is to mix the details with some personality: a small story from your day, a tease about what she will order, a joke about the venue. A run of messages that are all times and addresses looks like an errand, and it can look like you only care about the date.
Also keep your reply times natural. If she takes hours to answer, do not answer in ten seconds every single time. An hour or a few hours is a normal rhythm. That is not a game. It just shows you have other things going on.
Do not push when things are going badly
If she sends a flat or irritated reply, do not invite her out in response. When a chat is going badly, moving it forward tends to get silence. Get the tone back to easy first, with a light remark or a change of subject, and make the plan when she is warm again.
Avoid double texting too. If you send a good message and then a second one a few minutes later to fix it, you point out that you were worried. One message, then wait.
Move to a call if she is open to it
coach likes a short phone call or video chat before the first date. It helps you check whether you have chemistry, and it makes the date more likely to happen, because she has heard your voice and feels she knows you. Try "Want to do a quick call tomorrow so we are not strangers on Thursday?"
Know when to stop
Ask for the date once or twice in a clear way. If she says yes, lock in the time. If she keeps giving soft maybes and never suggests a time of her own, take that as an answer, and spend your time on someone who answers you.
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.




















