Here’s How To Feel More Comfortable Dating After A Breakup

Re-entering the dating pool after a breakup can elicit emotional responses ranging from excitement to anxiety-producing dread. The truth is that warming up to single life after a relationship is a process, and figuring out how to feel more comfortable dating after a breakup is an important first step. If the idea of dipping into the dating pool is giving you pause, it’s important to know that what you’re experiencing is totally normal.

“The dating discomfort experienced after a breakup is multifaceted,” Susan Winter, NYC-based relationship expert, tells Elite Daily. “Part of you is comparing the new person to your ex, and part of you is wondering how to frame the breakup when asked. Another part may feel tentative about [being vulnerable again].” Part of figuring out what’s holding you back from enjoying singledom is making sure you’re actually ready to start dating again. Although it can be tempting to rush into a new fling after saying goodbye to your ex, taking time to process a breakup is key. “Make sure you’re ready to move forward,” suggests Winter. “If you haven’t emotionally processed and packaged your past relationship, don’t even think about starting a new one.”

If you’re wondering whether or not enough time has passed since your last relationship ended, Winter recommends listening to your gut. There may be a totally valid reason why dating again doesn’t feel right, and you owe it to yourself to figure it out. “You’ll know you’re ready to date again when the thought of meeting someone new excites you,” says Winter. “You’ll be able to imagine a positive outcome and find yourself hopeful about the prospect of meeting new people.” On the other hand, if you can’t imagine yourself enjoying the process of meeting other matches, then you may need a bit more time to work through what happened between you and your ex.

Labelling your emotions can help you feel in control so you can deal with them in a healthy way.

Once you feel good about the prospect of getting your mingle on, planing out how you want to talk about your past relationship with dates can help you manage any lingering discomfort. “Prepare to be asked about what happened,” says Winter. “Obviously your new date will want to know how and why your relationship ended as a part of their own knowledge base, and that’s only fair.” There’s no need to go into too much detail before you’re ready, but being prepared in case the topic comes up can help. Even if the breakup was messy, making it clear that you’re over it is major. “Clearly, concisely, and diplomatically provide a two-sentence answer that’s gracious and positive, even if the breakup was bad and your partner was horrible.”

Lastly, letting yourself believe in love again is a great way to stay positive while transitioning back into dating. It’s so easy to feel jaded after a bad breakup, but succumbing to negative thought patterns can have a huge impact on your future relationships. No matter what went down between you and your ex, treating those experiences as learning opportunities can make a huge difference. Just because a relationship didn’t work out, doesn’t mean you won’t find love again in the future.

“You created a relationship before, so you can also create one now,” says Winter. “Just because it didn’t last doesn’t mean you didn’t do a good job. You should have confidence that you can believe in yourself again.” If your confidence took a major hit during your last relationship and you’re still reeling, take as much time as you need to recover. Feeling secure in who you are can help you attract someone who’s on the same page.

Dating after a breakup might feel strange for a bit, and that’s OK. The best thing you can do for yourself is make sure you’re ready to be vulnerable again. Any residual discomfort you feel about dating will pass with time. Remember: These big emotional shifts may not happen overnight. So, while you’re adjusting to single life, staying positive and honoring your feelings can help you move forward.


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Why You Should Consider an Age Gap Relationship

Have you ever considered pursuing an age gap relationship? Sometimes, your go-to response might be to date someone that is close to your age, but why not date a person that is younger or older?

In fact, some of the best relationships out there are between people that are not the same age, so this should further encourage you to pursue the same.

The key to any strong relationship is compatibility and attraction. Worrying about an age difference with your partner should be one of your last things on your mind.

Using dating applications

Blogger Updating Her Post Inside WordPress

Dating in this day and age often revolves around the internet, and that is why there are a wide number of dating apps, geared towards different interests.

If you are a younger male, for instance, that is interested in dating an older female, you can find the best dating apps by reading reviews on Beyond Ages.

Sometimes, the hardest part of being interested in a relationship whereby there is a large age gap between you is finding the right person to date in the first place.

This is where online dating can make the searching process a lot easier, and it also helps you realize that there are many people that are interested in these types of relationships in the first place.

Interesting conversations

There is a high likelihood that when there is an age gap in your relationship, the type of conversations that you will have will be far more interesting.

When you talk to your partner, you always want to learn more about them, but what if the conversations are so profound that they end up inspiring you?

Also, as you come from different generations, you might find that you know more than your older partner when it comes to particular categories of conversation.

This can also work the other way round, when they teach you about the world they know, for example how to sort out taxes. Both of you can educate each other on different aspects of the world you know.

Shared interests

Romantic couple kissing during evening at the beach

To make a relationship work, it is vital that you have similar interests that can ignite conversations and result in you spending quality time together doing something you both love.

This could be anything from dancing and yoga, to painting and reading. Whatever it is you love, if they love it too, just because they are older or younger than you, it shouldn’t mean that a relationship couldn’t work.

You might actually find that you have more shared interests with someone who is older than someone your own age. Quite often, it is a personality that can attract someone, and if you know the two of you will get on, it is the much-needed spark that a relationship needs to start.

The experience they have will benefit you

Dating someone that is older or younger than you could provide you with fresh perspectives on situations that someone your own age might not have considered.

Age can make a difference in how someone sees a situation based on the experience they’ve had, and as a result, they can offer alternative solutions as well as fantastic advice that you simply didn’t think of yourself. It can work just as well both ways and is quite often why an age gap relationship can be one of the strongest romances.

An older woman or man has had far more experiences than you, and as a result of this, they have more stories to share. They are more confident in themselves and their personality.

When you date someone older than you they can help you to discover more about yourself and what you can do, due to their confidence. So why wouldn’t you want to be around the type of person that is sure of who they are and radiates positive energy?

Levels of maturity can be different

romantic dinner for two

Just because you are younger doesn’t mean that your level of maturity is the same as every other person your age.

Some people in their 20s are more mature and ready to settle down, which is why the appeal of an older partner who is quite often at the same stage too is perfect for them. Remember maturity derives from what you have done in your life up until that point in time.

For instance, older women might date younger men because they love how youthful they make them feel, whereas younger men might like older women because they are more mature.

Becoming a mentor

If the idea of having someone to guide you through life appeals, then you should highly consider an age gap relationship. Your older partner can be there to help you as you become an adult and, in turn, you can help them to feel younger.

Dating someone that is younger than you might make you feel more youthful due to your partner’s energy and almost fresh life appeal. Their youthful nature might persuade you to do different activities that you might never have considered before you met them, and vice versa. You could also discover a new hobby or film that they love.

Having someone in your life that not only provides support but also is there to help you figure out adulthood is something that you can only really find from dating someone older than you.

Even though there may be many older people in your life, from your parents to grandparents or older friends, the connection the two of you have can help you in situations that your parents or grandparents simply can’t.

Age is just a number

round Timex analog clock at 2-33


If you are still worried about dating someone with an age gap, just try to remember that age is nothing more than a number. Whether you are 25, 35, or over the age of 40, when you are attracted to someone and care about him or her on a deeper and personal level, you start to forget about the age factor. Instead, all of your attention should be focused on their personality and how they make you feel when you spend time with them.

Even if you are at slightly different stages of your life, if the person you are seeing is important to you and you want them in your life, you can make it work.


Make sure you’re happy

The most important thing to remember when you are considering an age gap relationship is your happiness. As long as your happy it shouldn’t make a difference in the age gap.

Don’t take any notice of people making negative remarks towards you, they don’t know the ins and outs of your relationship, and you shouldn’t have to sacrifice your happiness to please others.

As this article has explored it, age shouldn’t make much difference in your relationship. However, always make sure that you are dating for the right reasons, the benefits aside, if you are dating someone who makes you smile every single day or makes you feel loved and you enjoy spending time then you know it is worth pursuing.

Don’t focus on whether they are older or younger than you. Even if there is a 10 or 20-year age gap, all that you need is a spark to further develop that relationship.


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

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Sun Stories: Trinity – Chapter 2 – Ghosted

I was stoked. Trinity had this vibe she gave off that was electric. Just the way she spoke, and the way she moved in the salon.

I knew this girl was special. Maybe not for me but just special in the world. She had such great energy, I knew despite her struggles, she had risen above. Like me, an over achiever with low self-esteem, that became the cream that rose to the top. The shining star in an enormous company. I had made that journey myself and I could feel who Trinity was and what she HAD to accomplish.

I knew she had a boyfriend. He’s probably a great guy. He lives in Boston and was cool with letting Trinity go to Philly and make her way.

I like him already. (That’s a secure guy that lets his bird fly to pursue her dreams and is confident enough in himself and their relationship to let her go.)

I love this dude.

I’ve been through this scenario already with Michelle, when Delaware Dave was trying to reclaim his high school sweetheart. If you read Michelle, you’ll see how that went. (See: Michelle – A Brand New Day)

I don’t want to hurt Boston, but Trinity feels like Michelle and I love how I feel when I’m around her. It feels like Michelle without the commitment so there’s blood in the water.

Let’s see what happens. I’m happy to be alone now at my age, but the old lion is always ready to get up for a good chase. (Still hanging in there with Cherie, but because of time and distance it’s been strained)

I can’t help it.

I text her.

Trinity is new to Philly and has zero friends and has made that clear.

A gazelle on Serengeti.

We’re supposed to meet at Square 1682 for the hookup drinks, but fucking Church and Amelia want to hang. It’s cool… Bros before Hos. (See: Church – Brand Ambassador and Amelia – New Hire)

I love them both. Church is a dear friend and Amelia is my hire, and I love hanging with them both on Monday evenings.

It’s like… Our night.

I know Trinity said she’d be available Monday night for my Square 1682 hook up, but my man, Roman isn’t working so I’m screwed that night. (See: Roman – Rock and Roll Bartender)

Which is fine, I’ll push Trinity off to Tuesday or Wednesday when he’s on. I’ll go to Marathon with Church and Amelia Monday and meet up with Trinity on Tuesday or Wednesday. Easy enough. The iron is still hot, and she needs friends and social time.

I text lovely Trinity the following:


“Hey I can’t do tonight, but Tuesday or Wednesday evening would work. (Free drinks!)



“I’m sure you’re busy with all you friends… but let me know if your want to hang at Square 1682 tonight or tomorrow?”

A week goes by and it is absolutely heartbreaking crickets.


I have mad energy for Trinity and for her to disappear is heartbreaking to me.

It’s just how my mind works.

I’m actually angry at the salon and tell Amelia all about it. I’m so mad that I’m not getting the dopamine drop I was expecting I go through withdrawal. (This tells me something about myself)

Amelia tells me to settle and now worry about it. (She’s so chill and amazing) But I’m so pissed and confused I just decide that while she works the front counter, I’ll just run around and clean beds and do laundry.

Where’s my Trinity? What happened? I know she works a lot and I like an industrious gal, but why has she simply disappeared?

I check her visits in the system and she hasn’t been in since our last encounter and number exchange.

I always worry, (as charming as I am) that maybe I have run off one of these pretty young girls.

(Never happened)

But where is “Stranger in a strange land” Trinity?

What happened?

I really like her and we had an amazing vibe.

I just don’t know….


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

Buy Phicklephilly THE BOOK now available on Amazon!

Listen to the Phicklephilly podcast LIVE on Spotify!

Instagram: @phicklephilly    Facebook: phicklephilly    Twitter: @phicklephilly