How To Start Dating Again After a Breakup, Divorce, or Dry Spell

Whether you’ve been off the market for a few weeks, months, years, or decades, getting back out there is no easy feat, especially if you’re not confident about how to start dating again. Common sense might urge you to be vulnerable, open yourself up for possible rejection, and be okay with the notion of kissing a few frogs in the process of finding a compatible partner. Sound intimidating? No problem if so, because it can be intimidating.

The mere thought of going out on a date after a rough breakup, divorce, or extra-long dry spell might induce feelings of anxiety. Because, for one, where do you even start? Sign up for a dating app? Hire a matchmaker? Slide into people’s DMs? Theoretically, any of those strategies could work, but to help you feel extra-confident in your intention to learn how to start dating again, a few experts share their advice below. Keep reading to snag their top tips for getting back out there, once and for all.

Your 10-step guide for how to start dating again

1. CLOSE THE PREVIOUS CHAPTER

Perhaps it should go without saying, but before you return to the dating pool, you need to be over your previous relationship so you can officially close that chapter in your life. Without taking this prerequisite step to finding new connections, you run the risk of either getting stuck in the past or bringing that emotional baggage with you on your dates.

“Turn the page, move on to the next chapter,” says Tammy Shaklee, relationship expert and LGBTQ+ matchmaker of H4M Matchmaking. “There is more to the story: Your long life is a series of chapters, with some more joyful than others and some more tragic. But keep turning the page and grow based on what you have experienced and learned.”

2. TAP BACK INTO WHAT YOU LOVE TO DO

When you’ve been in a relationship for a long time, it’s likely that you may have disconnected, at least in some sense, what you personally love doing with what you enjoy doing as a couple. That’s why Shaklee recommends reconnecting with yourself and writing out a list of what brings you, and you first, joy. Maybe it’s riding a bike, going to the farmers’ market, cooking a new recipe for dinner, or something else. Not only will this practice help you come up with fun date ideas, but it can also help you identify common interests you may have with potential partners.

3. FOCUS ON SELF-LOVE

Before considering how to start dating again, focus on finding self-love, because you can’t love another person without first and foremost loving yourself. “Love who you are today,” Shaklee says. “Cherish your tenacity on your journey. Celebrate who you have become through the many chapters you have experienced in life. Remind yourself that you are an eligible single.”

4. GET CLARITY ON YOUR NEEDS

Starting to date before you’ve gotten clear on what you’re looking for in a partner is like driving around without knowing where you’re going. Before you go out on your first date, relationship coach Laurel House recommends getting clear on your non-negotioable needs in a partner and a relationship. To that point, she notes that there’s a big difference between needs and wants: “Needs are what you actually need, or else the relationship will fail,” she says. These may include feeling safe, sexy, and seen, and able to participate in two-way communication. Wants, such as physical characteristics, for example, are like the cherry on top; they’re nice, but they’re not a required part of the foundation of the relationship.

5. TAKE YOUR TIME BEFORE GETTING OUT THERE—BUT NOT TOO MUCH TIME

Rushing into dating again before you’re truly ready is not a recipe for success, House says. You may still be holding on to negative emotions from your past relationship which may come across on your dates with potential mates. So don’t be afraid to take your time with getting back out there. That said, don’t wait too long. Not feeling ready yet can quickly just become an excuse that holds you back from your romantic future and destiny. “Some of us feel lonely in our box, but we get so comfortable that we are afraid to leave it,” she says. So, give yourself a deadline and do your best to stick with it.

6. GIVE YOURSELF PERMISSION TO START DATING AGAIN

So you’ve healed from your breakup and stepped up your self-love quotient—now what? House suggests giving yourself permission to start dating again. To do this, get out a real piece of paper, and write yourself a permission slip to go out on dates. This may sound very simple and even silly, but oftentimes, people feel they need to wait for something external or a sign to green-light their choices. In actuality, though, all they really need is to decide for themselves.

7. THROW THE DATING RULES OUT THE WINDOW

If it’s been a heady amount of time since you last dated, don’t feel like you need to catch up on all the current dating rules. “Don’t do what you think you should,” House says. “Instead, do what feels good and right to you.” Let your intuition guide the way.

8. KEEP THE CONVERSATION LIGHT AT THE BEGINNING

Divulging your entire life story on the first date? Perhaps not the best idea of all time. Shaklee suggests keeping the conversation on the first few dates focused on lighthearted topics and to wait until the fourth date to share about more serious things. “You do not want to scare off the other person by sharing too much (or asking too much) too soon,” she says.

9. TRY ALL THE DIFFERENT WAYS OF MEETING PEOPLE

If you’re serious about learning how to start dating again, House recommends not leaving things up to chance and using every possible avenue to meet new people. Try dating apps, in-person meet-up groups, working with a matchmaker, signing up for a class that interests you, or even making yourself available to connect with someone while you’re in line at the grocery store. And use your personal network, too. Don’t be afraid to be vulnerable and let your outer-circle friends know that you’re single in case they know of anyone.

10. PACE YOURSELF

Dating is a not a sprint to cross some finish line. It’s a process. It takes time to first find the right person, and then get to know them. That’s why Shaklee recommends finding joy in the process rather than trying to rush it. “Even if it ends up not being a romantic or love connection, perhaps you will meet a new buddy,” she says.

 

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

Listen to Phicklephilly LIVE on Spotify!

Facebook: phicklephilly       Instagram: @phicklephilly       Twitter: @phicklephilly

15 Smooth Pickup Lines For Dating App Matches That’ll Get Replies

One of the toughest parts of the dating game is keeping the apps feeling fresh. It’s difficult to come up with smooth pickup lines for dating app matches that would actually get replies. Luckily for you and I both, I was on the apps for long enough that I managed to master the art. And now I feel as though it’s my duty to you, dear reader, to share some of my best pieces of wisdom.

The trick to crafting an absolutely perfect opening message on a dating app is to understand first what you’re looking for with this experience. Some pickup lines work extremely well if you’re trying to just hook up with someone. Others are great if you’re trying to just start a conversation and see where it goes. Then, finally, there are the ones that could lead you towards something a little more substantial — they’re relationship-material and shouldn’t be deployed unless you’re open to a potentially deep connection. No matter what you’re looking for, I have got you totally and completely covered, my friend. Charge your phone before you read these because it’s about to start blowing up. Ready?

If you’re looking to get to know them better…

Indoor photo of satisfied teenage girl texts on cellular, reads interesting article online, wears casual outfit, creats new publication on own web page, isolated over brown studio wall with free space

Shutterstock

OK, let’s say you’re attracted to this person but you’re not getting a whole lot of intel on who they are based on the two grainy group pics from college and the empty bio that comprise their entire profile. You’d like to get a better sense of who this person is before you commit to spending (at least!) an hour of your life hanging out with them IRL, so I’d suggest you initiate a conversation with one of the following questions to give you some more intel on their personality:

1. “Ready for a game of ‘F*ck, Marry, Kill?'” Games are a great, light-hearted way to get to know someone a little better.

2. “It’s Friday and you just got off work after a long week. What’s next?” This question can be a huge character tell and, honestly, a great way to weed out people who may not be a great match for you right off the bat. If you’re a super social person, you’re probably not going to do well in a relationship with someone who wants to spend the weekend in their apartment binge-watching shows alone. Might as well get it all out there from the start.

3. “If you could quit your job and do anything with your life, what would your next move be?” This is a great way to tap into someone’s dreams to see if they at all align with yours. Your dreams, of course, don’t have to be the same but it’s a great way to see what the person is truly passionate about.

4. “What would you do if you won the lottery?” This question helps you get to know the person on so many levels. First, you get to see how they handle money (are they savers or spenders?). Second, you get to see what they choose to spend their money on, which can offer you some pretty great insight on what their values are.

5. “Where was that third pic taken? It looks amazing.” Asking about your match’s adventures is a surefire way to get them talking.

If you’re looking for a quick hookup…

Let’s say you want some no-strings-attached fun. You’re not looking for anything serious, you just want to get laid. Or, at the very least, get a solid make-out sesh in. Your best mode of operation here is to be as up front as possible with one of these straight-forward messages:

1. “You’re hot.” This is not the sort of message you send someone when you’re trying to build a lasting, meaningful relationship. It’s saying you’re only interested in one thing about them and it largely has to do with appearances. But it’s also making your intention clear while also flattering them. Win, win.

2. “So, what are you looking for on here?” Rather than blurting out, “Are you DTF?” this opening line puts the ball in your match’s court. It implies that you’re pretty direct and have a goal in mind. If you want your hookups delivered almost as quickly as your Seamless orders, this line could be a winner for you.

3. “You wanna come over and not watch a movie?” This is funny but it also makes it clear that you’re not just trying to, like, go on a date.

4. “I’d love to kiss your lips.” Kinda sweet, no?

5. “Hey sexy.” This strikes up a conversation with your mutual physical attraction right at the top. Warning: It might get steamy.

If you’re looking for something more substantial…

Whether it’s because you’ve just never been a casual dater or because you’ve casually dated so much that you’ve finally hit your limit, the fact of the matter is you’re no longer looking for something light and easy. You’re officially now only interested in finding the real deal and you can find partners who are also interested in finding that by sending the following messages:

1. “What’s your schedule looking like this week? You seem like someone I’d want to hang with IRL.” First of all, hanging out IRL is no easy feat these days — so that’s impressive. Second, this message is cutting to the chase. It’s not dilly-dallying and it’s not getting you in the dreaded text loop where the two of you chat for weeks on end but never ask each other out. If the person is down, you’ll go on a date. If not, you’ll move forward without having wasted your time.

2. “You free [day of the week you have something going on with friends]? I’m going to this [event] and would love a date if you’re down!” If this person is going to be a serious partner, you’re going to have to make sure they’re able to keep up with your friends and family. So why not throw them in the line of fire right off the bat? Invite them to an event you have going on and see how they react. If they’re down to tag along and act as a great date, you may have just found yourself a great potential partner.

3. “I’m looking for something serious, does that at all interest you?” If you’re looking for something serious, it’s important that you’re only talking to people who are also looking for something serious. One of the best ways to do that is by just asking right off the bat. If someone doesn’t respond, avoids the question, or just blatantly responds that they want something casual, then you can move on with minimal time wasted.

4. “It’s this exact day in the year 2045. What are you up to?” A huge part of being in a serious relationship is having similar goals and values. There’s no quicker way to find out what a person’s goals and values are than asking them what their life is going to look like almost 25 years from now. Are they married? Do they have kids? Do they think they’re going to be dead because the world is ending? Get a feel for whether or not they’re worthy of a substantial relationship by asking this question.

5. “Favorite Netflix show? GO.” I mean, let’s face it. If you wind up dating this person, a lot of what the two of you will be doing together is lounging on the couch watching shows. So why not make sure you’re into the same stuff right off the bat?

OK, now go forth and swipe!

 

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

Listen to the Phicklephilly podcast LIVE on Spotify!

Instagram: @phicklephilly    Facebook: phicklephilly    Twitter: @phicklephilly

Alicia – Chapter 6 – Sigh…

I waited a day and then texted Alicia. (Didn’t want to seem to urgent. I’ve been playing the long game on this girl.)
“Hi Elisha. Hope you’re having a good day!” (Then I sent her my contact information)
Crickets.
I go into action. I email the GM at Square 1682.
Jason,
I spoke with you two weeks ago about a special lunch I wanted to have with a client that is dear to me. I told you how she can only have lunch at 11am because she comes in to work early..
She has a love of French Toast. I’ve sampled the french toast at Square and it is exquisite. I know your breakfast ends at 10:30, but if you could hold it out until 11am on Thursday, March 22 i would be eternally grateful. 
Elisha is an integral part of my financial team and just happens to adore french toast and if we can bring her the Square 1682 experience I’d be eternally grateful , Jason.
He responds.

Charles,

We’re set to have you for breakfast at 11am.

Aside the French toast, is there another item that you’ll be ordering?

Chef team needs to break down the line to reset for lunch but they will keep whatever items you need on the line for your order.  

 

 

Thank you so much, Jason! I’ll just order something from the lunch menu. The french toast is just for her.

Thank you again! You are awesome!
Respectfully,
Charles

 

 

No problem. The General Manager, Chris, will be here that morning.

He’s looped in along with the chef team. We’ll see you then.

Six days later I go to my credit union to deposit a check. It’s around 2 in the afternoon. Alicia isn’t there. I send her a text.
“Hi. I’m at PFCU. Are we still good for lunch on Thursday at 11?”
Crickets.
That night at 11pm I screenshot the response from Jason about how their ready for us on Thursday with delicious french toast for her at 11am. I also include this text.
“The GM at Square 1682 has confirmed that we’re good for Thursday. I haven’t heard back from you. I know we’re having crazy weather tomorrow (March snow!) but please let me know for 11am Thursday. It’ll be fun!”
I get my very first text from Alicia the next morning. (It’s been over a week since I hatched this plan.)
“Hey sorry I haven’t been responding. I’m actually on vacation and won’t be back in Philly until next week so I’ll be in touch when the next time we can do brunch!”
I respond 3 hours later.
“No worries. Being away from Philly right now is a good thing. It’s snowing like crazy!”
I email Jason and tell him that for now, it’s sadly…off.
I don’t want to get disappointed and we are having a huge snowstorm right now, so I’m going to sit tight.
I suppose my next move will to simply return to the credit union next week. I’ll make another deposit and chat with Alicia and try to reset our lunch date.
This story isn’t over. I’m determined to get to know her and get her some delicious french toast.
Onward and upward!

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

Listen to Phicklephilly LIVE on Spotify!

Facebook: phicklephilly       Instagram: @phicklephilly       Twitter: @phicklephilly