I want to ask her out, but she’s recently single. How do I do it?

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Acridite asks:

I have liked this girl all through highschool and now after highschool she has broken up with her BF (of about 2 years)and I want to know if it is good to ask her out or to wait, and if I do ask her out, how should I go about it?


Demetrius says:

Here’s the two questions you’re posing:

  1. Is it okay to ask her out now, or should you wait?
  2. How should you go about asking her out?

Here’s your answers: Yes, absolutely it’s okay to ask her out, and the way you’d ask her out is the same way you’d normally ask a girl out. Totally depends on your style, your level of relationship, and the situation you’re in. Now, if you’re in a rush to get back to holiday shopping or some other thing you’re busy with, by all means, enjoy the rest of your day. Thanks for stopping by! If you’re thinking “Wait, I need to know how you got your answer” please, have a seat and let me elucidate.

The time-frame for when someone is truly over a breakup is different for each person, some people take longer than others, but, let’s be real here, there are few instances when that should factor into whether or not you should ask someone out. Day after a breakup? Sure, that’s bad form and way too early. A week after a break-up, okay yeah, that’s pushing it. Beyond that, you have to seize your opportunities where you can get them. If it’s a friend who you are close with, feel free to take a little more time since you can always circle back later and ask them out, or at least make your romantic interest clear. If it’s someone who you know casually and might not see for a long period after that, you might need to shoot your shot when the opportunity presents itself. Don’t wait for a prescribed time-frame based on the length of their previous relationship, because there isn’t one, and just make your intentions clear.

Now, I’m telling you to take your opportunities when they present themselves but how you seize your opportunities is up to you. I’m a situational flirt, and if I’m in your situation or any situation where I’m interested in someone, depending on the details my approach will change. When considering a newly single woman I’d ask a few questions: Was it a several years long relationship? Are we close friends, acquaintances, or is she just somebody that I used to know? Will I see her regularly, or never if I didn’t put in the effort? If this is someone I know and consider a friend, I might give her some space, and never clearly say, “Let’s go on a date” instead saying something along the lines of “When you’re ready and if you’re interested, I’d love to take you out. Cool if you’re not interested in me romantically though, no pressure”. If it’s someone I don’t know that well, but I know is recently single who I’m not sure if I’ll see again, I would be a bit more direct. In your case, since I’m missing some pertinent details, I’d lean more toward being direct since coy doesn’t work if you don’t get to follow-up. Even if she’s not 100% over her Ex, a month is a big enough separation where even if it’s a bad breakup, she’s not exactly sitting at home in the dark watching rom-coms wondering where things went wrong. One would hope at least.

Chat her up, let her know that you’d be interested in taking her on a date, give her your number, and see where things go. Worst case scenario she’s not interested, or not ready to date, in which case you can comfortably remind yourself that you gave it your best shot. Best case scenario she’s the one, happily ever after,thank me later, et cetera, ad infinitum, 

Good Luck Out There.

Demetrius Figueroa

Demetrius is a sex, dating, and relationship writer based in Brooklyn.

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