How do I make sure my old schoolmate knows I want to date her?


CitizenLuis asks:

So I (20m) went to school with this girl over year ago, I had always thought she was kinda into me but by then I was too busy trying to solve things with my ex. Through all this year we’ve texted a couple of times, not really passing from 4 texts each time, I always tried to be kinda flirty-really friendly to keep my options open. I was really surprised when She started trying to make plans with me like 5 times around November to February, but for one thing or another we couldn’t meet up, I’m starting to like the idea of being her boyfriend, but how do I ask her out making really clear that it’s a romantic date and not just a friend invite? Last time I invited her to something she responded really happy but I want her to be sure of my intentions

I’m 90% sure she likes me but is it a bad sign that she had sometimes called me “Dude”?

Demetrius says:

You know, I could spend this whole post writing about this quirk in the English language, especially the American variant of English, where you can call both men and women “Dude”, “Bro”, “Guys”, etc. and no one bats an eye. Another topic for another time I suppose. Anyway, I probably wouldn’t read too much into her calling you Dude because it’s just a quirk that English speakers in America have. I don’t think it’s a sign that she only sees you as a friend, so it probably means exactly nothing.Or does it!? No, it doesn’t, but I’ve been dying to use an interrobang for so long on the blog, so here we are, at the mercy and whims of your humble writer. Moving on…

Here’s the thing I want to know, if you’ve been texting off and on for all these months, why haven’t you met up yet? I’m not even talking about setting up a date, or making your romantic intentions clear, I’m just talking about getting a coffee or something. How can you try to hang out with someone for 4 months and not see them? Is there a lack of effort on your part or what? It just seems weird that you like her, she’s tried to make plans with you, and you still haven’t hung out. the math isn’t really adding up here and I’m not sure if it’s because you lack initiative, or she’s just not following through but, get it together here people. It’s possible that she’s the one that constantly flakes, so every piece of advice that follows could be pointless. If that’s not the case and the reason you haven’t met yet is because of inaction, or lackluster initiative on your part, you need to be more proactive.

Another thing to address, and I’ll chalk this up to you being 20 years old and infatuated. Why are you starting to like the idea of being her boyfriend if you haven’t seen her in what I assume is close to a year? What is the basis of your attraction, besides her attractiveness? You said yourself that you’ve texted “a couple of times, not really passing from 4 texts each time” so it’s not like you guys are having these long conversations where you learn, grow, and connect with each other. There’s nothing wrong with being infatuated with someone, nor with being primarily attracted to them physically, but just be clear on what your motivations in dating are. I don’t think you should rush to be her boyfriend, since you have no clue what she’s like on a first date, so maybe dial that misplaced enthusiasm back a bit.

Okay, enough chiding you, let’s get down to your central question. You’d like to know how to make it clear that you’re interested in her romantically. This is going to sound crazy, but just hear me out because I’ve given this a lot of thought and I know one fool-proof method to be sure that she understands that you are interested in dating her: Ask her on a date.


I know, I know, it’s pretty outlandish but just roll with me on this. If you use the words “I want to take you on a date” I think it’s safe to assume she’ll know you want to take her on a date. If you’re feeling brave, you can also say “I want to be clear, I’m interested in dating you, not just being your friend”. I know it sounds far-fetched, but if you tell people what your intentions are, they generally take you at your word. If you then follow those words up with actions, in this case taking her on a date that you plan, she’ll know that you mean exactly what you say. It’s really not more complicated than that. State your intention, plan a date, follow through with your date.

Beyond that, I’ve got nothing. I’d be concerned about not connecting earlier, and I’d dial back the enthusiasm a bit and definitely DO NOT lead with “I totally see myself being your boyfriend” because that would be too much too soon. Just ask her on a date, plan it, follow through, and take everything one step at a time.

Good Luck Out There.


One thought on “How do I make sure my old schoolmate knows I want to date her?

Your Thoughts?

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s