How To Reconnect With Someone You Already Know & Want To Date

This is going to sound painfully hackneyed and like I'm a try-hard at being a "chill-girl-who-is-also-wifey-material" but... I'm bad at one-night stands. To be fair, I've never had one. Getting it on with a stranger isn't in my wheelhouse, no matter how much the punk deep down inside of me wishes I could "DO WHATEVER" (pun intended). I prefer knowing someone before heading home with them. I like a long, juicy crush to rile me up. If you are wondering how to reconnect with someone you want to date, my advice is: get creative.

Maybe not deliver-the-avian-species-of-the-twelve-days-of-Christmas-to-your-crush-like-Andy-in-The Office creative, but thinking outside the box can in fact help you get into someone's box. In all seriousness, if you are looking to spontaneously run into that really adorable guy at the wine shop who helps you pick out the best bottle, there are ways to flirt outside of his place of work (yes, this is specific, and yes, I am plotting).

The "friend zone" is real. Especially with acquaintances and old friends, it's hard to know if there was ever some mini-crushing going on on both sides, you know? Here are a few creative ways to reconnect and find out if there were feels or if there might be in the future:

1. The Old "Finally Add You On Social Media" Trick

OK, so this isn't exactly outside the box, but randomly following an old coworker cutie on Instagram is a friendly nudge that says "I'm here and I'm cute too!" You don't need to wait until a friend-of-a-friend tags a picture of them to follow their account, in fact, you should seek them out at a very random moment in time.

It's like saying, "Yes, I thought of you and I Googled you and I found your Instagram." Life is short, so do things like this because why not? Once they see how great you are doing, you might even get a DM. Or heck, you might just DM them. Nothing is stopping you and the internet means that this is easy — so bye, get out of here, you have a friend to request.

2. Do Some Light Stalking

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I want to preface this recommendation by saying that real stalking is scary and you shouldn't do it to anyone, and you should not stand for someone doing it to you. That said, if you see on your Venmo feed that the nice person from your old intramural softball team is still going to "Turkey's Nest" regularly for beers, why not accidentally like their transaction? Then, immediately send a quick message saying "Oops! And also how are you?"

This is definitely a bit much, and would only work if you are already Venmo friends, otherwise it's too creepy, but hey, I said "get creative," right?

3. Poke Them On Facebook

I can't seem to quit the social media theme, but it's just such a readily available means of reconnecting. "Reconnecting" is the only reason parents have Facebook, after all. A poke is LOLz and if your crush is into you and a match, they'll probably think it's LOLz too. I like that a poke is vintage, just like you and this person's prior relationship.

4. Ask Them Out

I know! So simple. So straightforward. Is she even being serious!? Why yes, I am. It's 2018, and Time's Up in very serious ways, but time is also up on waiting around for your old crush to magically pop up on a dating app. People are busy. People are aloof. People are not thinking about all of the crushes they have had in their past. Do yourself a favor and shoot a text to the person you want to see. Ask them for drinks, if they are in a relationship, they'll let you down easy. (And if they don't they are a jerk and thus not for you.)

5. Tell Them You're Doing A Dating Experiment And Would They Like To Be One Of Your Dates? It's Anonymous

If this sounds specific, it's because I am in the middle of a podcast dating experiment/journey to self-acceptance/whatever, and an old college friend was one of my dates! This is taking things a bit further, but if you're actually in the process of going on a lot of fun and casual dates, let that be your confidence in adding one more date, only this time with a nice person from your past. I dare you.

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