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What Happened When I Asked My Exes for Dating Advice


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What Happened When I Asked My Exes for Dating Advice

To learn from past relationships, I asked three of my exes what I did right or wrong.

After a breakup, we usually don’t take the time to reflect on what went wrong or how to better ourselves. Instead, we send our former lovers off with a “good riddance” and before that door has completely closed, we move onto the next without hesitation.

I wanted to stop this common pattern. So I asked three men from my past – my childhood boyfriend, an ex-boyfriend and a guy I casually dated where the romance fizzled – for dating advice. Specifically, what did I do wrong? What could I have done better? What I thought would turn into a full-on bash fest where I’d encounter subliminal “fuck you’s” and carefully placed insults turned into an amazing learning experience. I received some sound advice on how to improve myself and be a better romantic partner in the future.

PLUS: My New Twitter Account Brought All My Exes to the Yard

Advice From My Childhood Boyfriend


DON’T be crazy.

When my childhood ex reminisced about our on-again/off- again relationship, he recommended that I turn down the crazy. One of the biggest mistakes I made in that relationship was turning into a raging, jealous…well, crazy woman.

One time I acted out irrationally when he took a trip to Miami with a bunch of friends. His flight was barely off the ground before I imagined him belligerently drunk, hooking up with two hot girls in a threesome, and having a wild and crazy fun time without me. And while we weren’t officially a couple, I took it upon myself to declare us an item while he was 1200 miles away, which only added to my paranoia.

After calling and texting him non-stop, causing unnecessary arguments and jumping to cliched conclusions, the damage was irreparable. When he returned from Miami he was no longer interested in continuing our romance. I had completely scared him off.

DON’T rush into a relationship.

My need to rush things and jumpstart our relationship prematurely hurt us in the end. Even though I knew we had amazing chemistry, we had a lot of issues that developed over the years that we never fully sorted out. I was more focused on the title and being in a relationship than taking the time to build a substantial relationship.

DON’T make out with his friends.

I know this sounds like a dead giveaway, but when angry or resentful we sometimes seek revenge on the guy/girl who broke our heart. Making out or being romantically linked with a close friend of an ex may “sound” like sweet vengeance in the moment, but take heed when chartering these dangerous waters. If your former love interest ever found out, it will not only destroy your reputation but also ruin some friendships.

DO keep things fresh.

My childhood boyfriend complimented me on how I often kept our relationship exciting. The little surprises, and how closely I paid attention to detail, came in handy when I wanted to ignite the spark in our relationship.

Advice From My Recent Ex-Boyfriend

I dont care

DO rep your man/girl.

Showing interest in your significant other’s hobbies, being loyal and trustworthy, showering them with affection, and showing support boosts your boo’s confidence. It also shows that you are 100 percent committed to the relationship, which minimizes insecurities.

DON’T be so guarded.

All three exes hinted that my guard was so high up that it was impossible to knock down my imaginary yet unbreakable wall. And while they weren’t bashing me for being cautious, my level of precaution worked against each relationship. The key with this tip is balance; know when to let your guard down and when to let others in.

DO live in the moment.

One of the bigger issues my ex had with me was my constant need for control, and how I’d get upset if things didn’t go “according to plan.” If I would have taken the time to live more in the moment, our relationship may have progressed more positively.

Advice From My Former Fling

talk like an adult

DO start what you finish.

Whether it’s an argument, sex, or a quick and random thought, always follow through. If you are constantly starting things but don’t finish them, it’s not only frustrating but you also look flighty, unsure of yourself and like all you do is play games.

MORE: How Breathing Techniques Can Help Couples Avoid Arguments

DO express yourself and communicate in an adult-like manner.

Whenever you are in a relationship, it’s important to communicate and be open with your partner. Just don’t be childish or petty while expressing yourself.

What could have turned out to be a complete and utter disaster helped me pinpoint things that I need to improve about myself. This project allowed me to take a step back, receive different points of views and self-reflect. Now, I know how to have a more meaningful and fulfilling relationships, and can’t wait to put these lessons to good use in the future.

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Tiffani is a true city gal, hailing from the concrete jungle of New York City. With a large coffee in tow (that’s pronounced caw-fee to my non-New Yorkers) this closeted “self-help” addict and Lifestyles writer is on a continuous quest to discover how to have the best romantic life. An old soul with new age sarcasm, Tiffani’s sharp, witty and tell-it-like-it-is attitude has resulted in many a snafu as she tries to navigate and conquer the most challenging and complicated assignment of all: dating the New York City man. Come a long for the ride as this seasoned serial dater tries to find balance between her journey to self-love and her old school values on dating and relationships. She writes about her lessons and adventures in dating as a twenty-something millennial and all the new rules that apply.


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