The Classiest Texting Introductions for Your Man of the Moment

When it comes to texting and dating being in the same category, females typically have a lot of questions. Is it possible to initiate communication with a guy without scaring him off or coming across as clingy? What are the limits? And if you make a move before he does, will he still take the reins?

The truth is, it doesn’t really matter who makes the first move. What matters more is how that move was made. If you develop strong communication skills- even in texting- your love life will thrive. Keep your introduction simple, light, and direct. Exude both confidence and femininity, so that your intentions about getting together are clear, but you are still letting him take the role of chivalry.

Sometimes the most eloquent women get “text-tied” or don’t know what to say when texting a guy, wondering if they’ll sound awkward or he won’t catch onto their carefully crafted joke of 140 characters. And you wonder, “Is using this emoji appropriate or is it too much?”  Digital communication can be complicated, but it doesn’t have to be. So, let’s score you a date for this weekend, while remaining classy and lady-like.

If you decided you want to start a texting conversation with a guy, which could potentially lead to a date, here are some pointers:


For the Bold Chica:

“You… Me… Friday night. Are you up for the challenge?” *insert silly offbeat emoji*

This text is extremely bold, yes. But, it shows some personality, and importantly, all men love a challenge. What is the challenge after all? He needs to respond to your text in order to find out. Guys take communication differently than females do. He isn’t going to overanalyze it. You can be silly, and he’ll love that.

For the Girl Who Just Wants to Remain Nonchalant:

Text him about some kind of information you need, such as homework or directions to a party, or anything that would seem relevant and not like a ploy to communicate with him. Let’s face it. Ploys like this are generally obvious. If he can do you some kind of favor, this is a good opportunity for him to feel masculine. It’s kind of like the old fashioned dropping of a handkerchief, but via text. Once you engage in conversation, start inquiring more about him and his weekend plans. If this leads to him asking you out, he was interested all along.

For the Genuine Girl:

“Hey, I’d love to get together Saturday if you’re around.” Then, you suggest a location.

This is one of the simplest lines out there, but it works. This suggestion comes best recommended after you have gotten to know a guy well or have been on several dates with him. Some guys don’t mind when women initiate. It can be sexy. Although, what most men would probably agree upon is that they need to be able to act like men. Your opening line is sweet and low-key, not indicating a pressured scenario in any way. So, see what he says.

For the Silly Girl:

“What are you up to this weekend? Let me guess…” *insert something unusual, yet humorous about his personality, interests, or what you know about him*

“I know you are playing nerdy tonight and working on Professor Shmo’s project.”

“I know you will float on over to Timmy’s house party to avoid working on Professor Shmo’s project.”

The majority of people with complex, multi-dimensional personalities crave banter in a relationship. What keeps us all interested and sticking around in long-term relationships is who the person truly is inside. And in this case- focus on bringing out your sense of humor. The traditional introductions of “Hey, what’s up?” and “What are your weekend plans?” are simply boring and do not guarantee any kind of response. This text pokes fun at him in jest, while remaining light and creating communication between the two of you. The more you open the door for banter with guys you are interested in, the more you can find out if the interest is mutual. Usually, if he has romantic interest in you, he will send a clever response. If he doesn’t- oh well? Maybe he’s not as creative as you?

For the Flirty Girl:

“I need to go shopping for spring clothes and could use a man’s eye, if you would like to tag along.”

*Picture message* “Hey you, I’m out shopping right now, trying on dresses. What do you think of this one?”

Either one of these messages create intrigue because he’s thinking about you in a feminine way. This text is not about shopping or showing him you are a fashionista. It’s about figuring out if he sees you romantically, or presenting yourself in a way where he would. Plus, think about it: if he doesn’t have any remote interest in going out with you, he’ll just be thinking, “Okay, why is she asking me to go shopping with her? I just met her. There are so many other things I could do.” Or, “Why is she sending me picture messages? I didn’t know we were friends.” In this case, keep moving forward because he doesn’t have a clue.

For the Quirky Girl:

Start a conversation which comments on a previous interaction between the two of you, or alternatively something about your life which relates to his. Examples:

  • “I’m here at that coffee shop we went to last week. They are out of soy milk today. I hope they don’t go out of business for this heinous crime.”
  • “I’m walking past the gelato bar you told me about. Would you be super-mad if I went in there without you?” *wink*
  • “My friend invited me to the contemporary art exhibit you are obsessed with… I think I’m obligated to invite you, too.” *silly face needed*  

One of the best life mottos about individuality is: “When in doubt, be as quirky as possible.” The key to this motto is to not try too hard. Think quirky within reason, as in- not totally bizarre.  Everyone has something just a little bit off about their personality, or something that is a bit unusual that other people don’t see. Let it out. When you are texting with a guy, it is definitely important to keep it simple and not throw in too many zingers. That’s confusing. But, just the right amount of quirky, offbeat zingers will make his day. From here onward, he will initiate way more than you do because he wants to know what you will do next.

For the Active Girl:

When you’re out and about, send this:

“Hey I’m here at *insert venue.* The *insert something unique about the place* is amazing. You should come out!”

The interesting aspect of this message is, your focus is not about him coming out to see you. If it’s a Friday or Saturday night, he probably already has plans. And that’s good. The most attractive people are generally active and in demand in different facets of their lives. What you want to know is whether he will suggest an alternate time to get together. If he does, then you probably have a date coming up, granted that he continues to seriously pursue the option and make a concrete plan. Why does this text work? You portray yourself positively as active and having a good time. You have plans, and are willing to include him on them, even if the timing of sending the message is unreasonable. And, even if it is unreasonable, if he likes you, you are going to find out by his response. Alternate suggestion = your next date.


Ultimately, you can initiate a texting conversation with a guy and not ask him out. But, if he is interested and up for taking the reins, your opening line may lead to him asking YOU on a date. Texting should be used for entertainment and logistics, so keep simplicity in all interactions. 

It’s all in your natural energy, which comes across in your communication. Any anxiety or insecurities will come through. Instead, portray confidence, standards, and your large capacity for fun experiences.