Here’s How To End Things With Someone You Weren’t “Officially” Dating

Here’s an interesting post by one of my female readers.

Several years back, I found myself grappling with a rather common conundrum. After casually dating the same guy for several months, I decided I wasn’t invested enough in the relationship to pursue it any further. But since we never decided it was exclusive, put a label on things, or defined the relationship in any way whatsoever, I had no clue what the protocol was. If you, too, are wondering how to end things with someone you weren’t “officially” dating, then know this: There’s no one-size-fits-all formula because how you approach it will depend on such factors as how long you’ve been dating, how serious things were getting, etc. However, experts say there are certain tried-and-true guidelines you should stick to when breaking off an undefined relationship.

According to Maria Sullivan, dating expert and VP of, and Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking, it makes sense why it might feel awk AF to call it quits on something that was never made official, especially if you generally avoid or put off confrontation.

“Everyone hates uncomfortable conversations,” says Trombetti. “And if you’re someone that hates to hurt anyone’s feelings or doesn’t like to disappoint, it never feels good.

That’s why it can be pretty tempting to dodge the conversation entirely. But as much as you may prefer to “Irish exit” your almost bae, experts agree the one thing you shouldn’t do is neglect to formally end things, no matter how casual your relationship was.

It's best to meet in person or call when ending things with a person you weren't official with.

Jovo Jovanovic/Stocksy

“You shouldn’t just let things fizzle out or ghost someone, because it makes the process of moving on a lot harder,” explains Sullivan. “It leaves a lot of questions unanswered and often people will begin to blame themselves for why things didn’t work out when it might have just been bad timing.”

Trombetti advises following the golden rule: Treat others the way you want to be treated. If you’ve ever had someone leave you hanging, you probably know it doesn’t feel so great. So, just as you would likely want the person you’re casually dating to be upfront with you, it’s advisable to provide your unofficial boo with the same level of honesty.

Of course, if the person you were dating has mistreated you or made you feel unsafe in any way, then you have absolutely no obligation to meet up with them in person or even call them on the phone. Your top priority should be to break it off in whatever way makes you feel comfortable and secure.

Otherwise, both experts concur that the best way to handle this situation is in person, or at the very least, with a phone call — particularly if you’ve spent a significant amount of time together. A text may suffice if you’ve only been on a few dates, but if you’ve been seeing each other for months, it’s best to call them up or make a plan to meet. A phone call allows the person you’ve been dating to hear your voice, which is a huge advantage over text because tone can play a major role in how they react to your decision. It also shows them that you care enough to engage in a two-way conversation and give them a chance to say what’s on their mind. On the other hand, if you decide to meet in person, you’ll want to be mindful of when and where you meet. In general, it’s best to choose a location where you can have a private conversation, which means a bar or a restaurant are probably a no-go. You can meet up at their apartment, or even offer to take a walk.

When I broke it off with my aforementioned not-quite-boyfriend, I asked him to meet me at a local park. I later found out that since this was an unusual place for us to link up, this tipped him off that something might be up, and he actually came prepared for the possibility that we might be ending things. I cut to the chase pretty quickly and simply told him, “I think you have a lot to offer, and I feel really lucky that you reminded me how I deserve to be treated by someone I’m dating. But I’m having trouble seeing a future here, and given that my life is about to get really hectic, I think it’s best if we go our separate ways.” To my relief, he took it super well — so well, in fact, that shortly after that, he supported my crowdfunding campaign for the album I was recording, and when we ran into each other a couple months later, we were able to exchange pleasantries with barely any awkwardness.

Breaking up with someone you aren't official with isn't easy, but it does offer closure.

Javier Díez/Stocksy

I can’t tell you exactly how to go about breaking up with someone you weren’t official with because only you know what feels right given your unique romantic circumstances. But I will say this: wherever, whenever or however you opt to end things, it’s worth having a plan for what you’ll say. If you decide ahead of time how exactly you’ll bring it up, you’re less likely to back out of breaking it off at the last minute. For example, Trombetti suggests saying something along the lines of, “I’m so glad I got to know you, but I just don’t feel like we’re right for each other” or, “I’ve had a lot of fun with you, but I just don’t see this continuing.” Starting with something positive may help to soften the blow, and following up with a super direct statement ensures that you don’t leave any room for confusion about the fact that the relationship is over.

“You should be prepared for the other person to be disappointed, and maybe even questioning why you made this decision,” Trombetti tells Elite Daily. “Don’t go off script and engage. You don’t need to get into the nitty-gritty such as ‘I am just not that attracted to you’ or ‘I find you to be a bit of a jerk.’ If you weren’t official, you don’t owe them those explanations — and let’s face it, your reasons are usually never going to sit well with them. It’s best to be kind, brief, and honest.”

So, here’s a recap. It’s best to end things either over the phone or in-person, depending on what feels right for your specific situation. Always have a plan for exactly what you’re going to say, and consider starting on a positive note, but ending on a clear-cut statement that you don’t wish to continue the relationship. Never feel like you need to over-explain yourself or justify your decision. While it may not be easy to break it off with someone you were never official with, it’s ultimately good dating karma. Remember: Having an honest convo is the best way to get closure, which is something you both deserve, even if your relationship wasn’t ever fully defined.


Thank you for reading my blog. Please read, like, comment, and most of all follow Phicklephilly. I publish every day.

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20 Questions to Ask Yourself Before Having a One Night Stand

1. Are you married, in a committed relationship, interested in someone, or religiously forbidden to have premarital sex?

Today’s society does not see marriage the way it seemed to be a hundred years ago. But it is the same. It is a sacred commitment between two people. The act itself will never change. How each person treats it, is what the problem is. And this should be a question you ask yourself before heading out to play in the woods. If you love the person you are with, you need to focus on that love life. Not going crazy over a few hours of pleasure that could have you losing it all. The same applies to the rest of the question, including being in a committed relationship with God. Such as a priest, nun, monk, etc.

2. Do you have an STD such as HIV, AIDS, Herpes, Warts, etc.?

Spreading this around is unacceptable. These STD’s already have a steadily increasing number in the world of sexual enjoyment. And if this is something you have, or think you might, then the partner involved you are thinking about DESERVES the right to be told. If they change their mind, that is that right, as well. With that said, you need to take care of you. What if you have one of these issues, and it flares up afterward?

3. Will you use protection?

Some do not care. They think since they are clean, all with be okay. What if you are having a random fling from someone you just met tonight, neither of you know each other, and you have to think that if they are so readily available for a good time, do you honestly think this is their first time? And are they thinking the same as you? For all safety measures, protection is best and even then, it’s not foolproof.

4. What if the condom breaks?

Name brand and how it’s never happened to you before does not matter. It can still happen. What then?

5. How well do you know this person?

This goes back to #3. A random person can bring you anything in the heat of the moment. Even a friend of twenty years can be carrying something Ajax is not able to wash off. Knowing someone does not seem to matter. In today’s day and age, everyone needs to apply for a weekly physical. With a medical form as proof.

6. What type of reputation does this person have?

This plays a part in your life. Being with someone for a moment, can greatly impact your life. Not even all men are patted on the back for taking on the local junky who does this as a lifestyle to support habits. And you girls, you know how it is harder on us. Everyone’s reputation is indeed a great concern to question.

7. Is this worth $100? (The cost of a hotel room)

That is if you do not go cheesy and use the backseat and maybe you can find a room for $55 but even then, is this two-hour adventure worth wasting your hard-earned money? Do you not have something else to buy for your car or home? Perhaps food?

8. How will I feel after?

If you are easily connected to people, you really need to stop here and do serious soul searching. To walk in, go at it, and leave with a guilty conscience, is a huge undertaking. What if you see it in their eyes that they are feeling bad?

9. How will they feel after?

As people, we are unique characters. We all proclaim we can do this and that. Walk away without looking back. The matter at hand is that most women feel scorned or used if the person they are with does not show interest in them anymore.

I know a once young man who had a one time fling with a young lady who proclaimed that is all she wanted. Turned out, she lied. She became obsessed and destroyed his truck to the metal with a set of keys.

10. What if they want more than you can give them, afterward?

This goes back to #9. Not even sure if this question should be here. Almost like a repeat. Due to the circumstances of what if, it is probably best I leave it be. This is about thinking it over before jumping. Twice, if need be. So, it stays.

11. What do you do if it’s starting but you find myself suddenly not interested?

Having no clue about a one night stand, this would end up being my luck if I attempted one. How would we all handle this? Personally, I would be stuck between a rock and a hard spot (no pun intended) but would stop it. No one should ever have to share their body if at any point their mood changes. Question is, this one-nighter, will they be as accepting? Lots of worms can fall out of this can.

12. Is this with a friend and if so, is it worth the chance?

The all too commonly heard do not mess it up friendship talk. Look, no friendship is worth losing. Good friends are rare. Why would you throw that away for? Some of us learn the hard way when making a bad decision but this one, having never touched it, can see how it could be even worse.

13. Do you work, go to church, or to school with this person?

Awkward!!!! Especially if you apply rather or not the person is married to someone you work with. Maybe your parents know their parents, and everyone joins for a Sunday dinner at the local restaurant for small chat. Wow! Now to worry if others can see what both of your faces are saying.

14. Is this person know to have an active sex life around town?

I admit. This is a wee bit redundant with this question. It can not be argued on how this question fits three others. Due to sexually transmitted diseases, it should be asked at least fourteen more times. It should be the top of the line question you ask yourself. For real. Is your body worth hurting?

15. Are they good friends with my siblings?

There is something about sleeping with your sibling’s best friend. Not only do most relationships in this area end, but it also kills the mutual friendship your brother/sister has with your one-night lover. While you may not have a broken heart about it once done, your sibling could end up not trusting you. The damage i can feel this could cause is significant.

16. Are they married?

This question is not for you only. Being as big of a question when asking if you are married, this one also goes with the risk of being caught and losing everything. Not only for you, but also them. Along with an outraged spouse from their end, chasing you down the road on foot to kick your butt.

17. Do you acknowledge them if you see them in public?

At this point, things are feeling a bit repetitive. Yet at each question, a new scenario is created. Like, for instance, what if this was not discussed and you both attend the same college together? Do you walk past each other as strangers, yet still catching a glimpse? Or maybe you turn and go the opposite direction? If this was not discussed, and they are headed to you with a huge smile, as you are holding hands with your partner, do not even attempt to run. You are busted! Might want to get to addressing this before that happens.

18. How will you feel about yourself later in life?

At the moment, you may not have any regrets. What though, if in ten years, you look back at the “mistakes” you made and place this one in that category? Maybe by now, you have heard how the person is in jail for killing their lover over jealousy, or they are now on crack due to being alone. Yes, this is a bit extreme as examples but this is an extreme decision. You must ask yourself how will you feel.

19. If asked had you ever had a one-time affair, do you tell the truth or lie?

Not talking about with a group of your same-sex friends. I am talking the partner you want to spend the rest of your life with. Do you actually come out, tell the truth, and hope it just goes away? It sounds to me like a #18 issue at this point. But if you know if you tell the truth, it will be used over your head, you have even bigger issues at bay.

20. What if you want to see them again, but they do not want to?

Truly you did not think you escaped the jaws of real emotions, now did you?

It seems no matter how strong we think we are when it comes to the intimate side of life, a crush, or infatuation, no one is exempt from feelings. And if you think it could happen, you know, falling for them … rethink what you are about to put yourself through.


Thank you for reading my blog. Please read, like, comment, and most of all follow Phicklephilly. I publish every day.

Buy my new book, Angel with a Broken Wing on June 20th, on Amazon!

Listen to the Phicklephilly podcast LIVE on Spotify!

Instagram: @phicklephilly    Facebook: phicklephilly    Twitter: @phicklephilly

25 Open-Ended Questions To Text Your Crush & Start A Conversation

So, you’ve got a crush on someone new. OMG! Those nervous, excited feelings are fun, but they can also be kind of stressful. How do you make a good impression? How do you get them to see you as more than a friend? It’s time to step up the flirting game, and open-ended questions to text your crush will help you learn more about each other. Hopefully, you can start a meaningful conversation that eventually turns into something more.

Like a lot of people, you might have some extra time on your hands lately — the perfect excuse to put your energy into a new flirtationship. Texting your crush can be scary, but it’s also the first step toward building a strong connection with them. You’d be surprised at how easy it is to open up when you’re not face-to-face (hello, Love Is Blind!) And hey, you never know where this conversation could go. Before you overthink it, go ahead and send one of these open-ended questions to pique your crush’s interest and get them talking.

1. Who are you closest to?

2. How do you feel about [world event]?

3. What are you most proud of?

4. What are you like as a travel partner?

5. What’s one thing you dream of accomplishing?

6. What does a typical morning look like for you?

7. What’s one thing you’ll never do again?

8. What’s your favorite place in the world?

9. Who do you look up to?

10. What’s the most spontaneous thing you’ve done lately?

11. What’s the most surprising thing about you?

12. What’s something totally dumb that makes you laugh?

13. How do you deal with stressful situations?

14. What’s one thing you couldn’t live without?

15. How would you want someone to describe you?

Westend61/Westend61/Getty Images

16. What would you do if you won the lottery?

17. What’s one controversial opinion you have?

18. Do you have any hidden talents?

19. What’s the last thing you listened to?

20. What skill do you wish you had?

21. What’s the luckiest thing that’s ever happened to you?

22. What book or movie has influenced you most?

23. What’s your biggest pet peeve?

24. If you could have anybody else’s life, whose would you want?

25. What’s your funniest memory from high school?

Before you know it, you’ll be engaged in a conversation you and your crush will both find super enlightening. It might help you realize things you have in common, which could lay the groundwork for even deeper life talks later on. Who knows? You could even have your own Lauren and Cameron love story in the works. You’ve totally got this!


Thank you for reading my blog. Please read, like, comment, and most of all follow Phicklephilly. I publish every day.

Buy my new book, Angel with a Broken Wing on June 20th, on Amazon!

Listen to the Phicklephilly podcast LIVE on Spotify!

Instagram: @phicklephilly    Facebook: phicklephilly    Twitter: @phicklephilly

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