10 tips for reconnecting with someone you dated briefly

We sometimes include products we think are useful for our readers. If you buy through links on this page, we may earn a small commission. Read our affiliate disclosure.

‍Sometimes we understand someone’s potential way too late, after we’ve already moved on.

Or maybe the timing simply wasn’t right the first time around.

Whatever the reason, you are not alone if you want to reconnect with someone you dated briefly, heaps of people experience this same problem.

The good news? I’ve got some great tips that will help you out!

1) Check in with them

If you’re hoping to reconnect with someone you dated briefly, the first thing you need to do is check in with them and make sure they’re open to the idea.

There’s no point trying to reconnect with someone who has no interest in rekindling a past relationship with you.

This may sound obvious, but you would be amazed at how many people try to reconnect with someone without having any idea if they still have feelings for them or not.

You don’t want to fall into that trap. There are a few ways you can find out if they’re open to reconnecting with you.

One option is to send them a friendly and casual text or email letting them know you’ve been thinking about them and hoping everything is going well in their life.

You could also get in touch via social media.

Now: I feel like it’s important to mention here that you don’t need to tell them right away that you want to date them again, you might want to just keep it very casual at first.

The good news is, if they aren’t interested in you at all, they’ll probably simply ignore you.

I know it sounds harsh, but ti’s the truth!

So if they reply and make conversation, you’re in luck!

Okay, now that you’ve checked in and got them talking to you, what’s the next step?

2) Find out what’s changed in their life

If you want to reconnect with someone you dated briefly, it can be helpful to get an idea of what’s changed in their life since you last dated.

This can help you figure out why you two weren’t a good match the first time around.

For example, you might have dated a woman who wasn’t ready for a relationship, but now she is.

Or you might have dated a guy who was struggling with his career.

Now that he’s got things figured out, he’d love to reconnect with you.

If you don’t know what’s changed in their life, the best way to find out is to have a casual conversation.

Start by catching up with them and asking them what they’ve been up to since you last talked.

This is important, as there might be things that happened since you’ve dated briefly that are now absolute deal-breakers!

For example, they could have moved, gotten married, or had a child.

This is the perfect time to find out if they’re still interested in you.

If they are, great!

If not, that’s fine too.

The thing is, try to not see this phase as “I need to get them to like me as soon as possible”, and approach it from a mindset of “Do I actually still like them?”

This has taken so much pressure off for me in the past and it has allowed me to have a lot more fun.

But not just that – if you approach this step from this perspective, you can actually figure out if you like them, or if you just like the romanticized idea of them that you have in your head.

You’d be surprised how often we don’t even have a great match with someone once we realize they are not who we idealized them to be.

Okay, now that you know what they’ve been up to and there still aren’t any red flags, it’s time to start talking again.

3) Start talking again as friends (and build from there)

If you want to reconnect with someone you dated briefly, you need to make sure you’re not putting too much pressure on the relationship right away.

If you’re both in a hurry to date again or have feelings that are stronger than friendship, it’s very unlikely the relationship will last.

Instead, try to build a friendship first. Focus on getting to know each other again, hanging out, and having fun together.

During this time, you can also think about whether you two are a better match for each other now than you were before. If so, you should let your friend know.

However, it is important that you don’t immediately jump into the dating.

There is a reason things didn’t go further the first time around – either you or your friend just weren’t ready.

It’s possible that things will be different this time around, but it’s not guaranteed.

As mentioned before, you need to make sure they’re still interested in you and vice versa.

If they’re still interested in you after all of this, then it’s time to talk about a date!

So, I’d recommend just keeping things casual at first and using this opportunity to really get to know them.

This can be really fun, as it allows you to see what your friend is like when they’re not in a relationship.

Or maybe you’ll notice that you’re no longer compatible with them and it’s best to end things before things get more serious.

Either way, the best thing you can do is just be honest with them about how you feel and what you want from a relationship.

If they feel the same way, then it’s time to take things to the next level!

However, be careful with that:

4) Don’t pressure them to date you again

If you want to reconnect with someone you dated briefly, you need to be careful not to pressure your friend into dating you.

This is a bad idea for a number of reasons.

If you pressure them into dating, then things can go downhill really quickly. This is especially true if they were the ones who ended things the first time you two dated.

If your friend feels like you’re pressuring them, they won’t be happy. This will make them feel trapped and pressured, and they might end things with you again.

So, if you want to reconnect with someone you dated briefly, make sure that you don’t pressure them into dating you again.

Now: usually, the transition from friendship to dating will happen naturally over the course of a few weeks if they like you as much as you like them, so if you just let things run their course, you might start to notice positive tension between the two of you.

This is a good sign that the two of you are ready to date again.

However, if you rush into it and immediately want to date them, they might be pressured too much, which can lead to them actually feeling overwhelmed and not having time to develop feelings.

Now: what can you do in the meantime to feel like you’re doing something?

5) Try manifesting them

Did you know there is a way you can try to reconnect with someone you dated briefly without being too pushy or desperate?

You can use the law of attraction to try to reconnect with someone you dated briefly.

This is a simple but powerful way to get a person back into your life.

Basically, you use visualization and positive thinking to create more of what you want in life.

So if you want to reconnect with an old love interest, you can start by visualizing yourself with them again.

There is an amazing ebook on how to manifest love, so if you want to get into more detail about how to go about this, I’d really recommend you give it a shot!

However, here are a few tips (some of which you will also find in the ebook):

You need to figure out your limiting beliefs. What is holding you back from truly believing that you can be with this person? Is it self-doubt? Is it something else?

After that, you have to be clear about what you’re really focusing on. Are you thinking about the relationship, or are you thinking about something else? Are there other things that are coming up as well?

Manifestation works best if you focus on one thing at a time.

You can use a journal to write down exactly what future you want with this person you’ve briefly dated.

Imagine what your relationship will be like.

Imagine what your life will be like.

See it as if you were watching a movie about your future.

The more often you visualize this, the more likely you are to actually manifest it into your life!

And the best part? Manifestation can help you build up confidence, which brings me to my next point:

6) Confidence is key

If you want to reconnect with someone you dated briefly, you need to be confident in yourself.

If you lack confidence and come across as needy, you may scare the other person off.

You don’t want to come across as too eager, but you also don’t want to seem disinterested.

So how do you find a balance between not being eager enough and not being too disinterested?

Well, being confident in your own skin is definitely a huge step in the right direction.

If you feel good about yourself and your life, the other person will feel that energy and be attracted to it.

This isn’t just about feeling good about your body or your bank account.

It’s also about feeling good about yourself as a person!

Self-confidence is not something that you can just fake.

However, there are some things you can do to help boost it up when you feel like it’s slipping away.

Taking care of yourself is a big one. If you take care of yourself unconditionally, you know that you’ll always have your own support!

Now: what if all that confidence still doesn’t seem to spark any romantic feelings in them?

7) If all else fails, be honest and let them know your intentions

If you want to reconnect with someone you dated briefly and nothing else has worked, you may have to be honest and let them know your intentions.

This might seem scary, but it’s better to be upfront than to let things linger for a long time.

Start off the conversation by thanking your friend for their time and letting them know you appreciate the friendship you have.

Then, let them know that you would like to date them, but you understand if they aren’t interested. Be honest and straightforward, but also be respectful and tactful.

This will put it all out on the table.

I know, it can be scary, but if you really want to date them again, you can’t be friends forever with nothing happening.

But before you do that, I have another important tip for you:

8) Try to understand why it didn’t work the first time around

If you want to reconnect with someone you dated briefly, it can help to understand why you weren’t a good match the first time around.

This way, you can work to improve yourself and try to avoid making the same mistakes again.

For example, you might have dated a great person who loved you, but you just weren’t ready for a relationship.

Now you are, and you can reconnect with that person.

Knowing why things didn’t work out at first can help you to actually convince this other person to date you again.

They might have thought they weren’t your type, but if you show them that you’ve changed, they might be more open to giving it another shot!

You can also learn from your mistakes and try a different approach.

The only reason this whole thing could possibly work again, is if you have both changed enough from the first time around.

If you’ve both changed, there may be a chance that it could work, if you take the steps I’ve outlined above.

Now, it’s time to be vulnerable.

9) Don’t be afraid to be vulnerable during your talk

If you want to reconnect with someone you dated briefly, it can be helpful to let them know about some of your insecurities and vulnerabilities during your talk.

Not only can this help build trust, but it can also show the other person that you’re human and you make mistakes too.

It can be scary to be vulnerable with someone you dated briefly, but it can also be incredibly helpful.

Be vulnerable about your emotions regarding them and the situation and don’t close yourself off.

If they can see how much you’ve changed, and how much you care about being with them, it can make a huge difference.

If you want to reconnect with someone you dated briefly, it’s not going to be easy.

But if you’re willing to put in the work and take the steps I’ve outlined above, then it could be well worth it in the end!

The thing is, some people might be put off by vulnerability, but that just shows that they weren’t ready for a relationship with you.

In that case, you dodged a bullet! So, if you’re vulnerable and they react in a good way, that’s amazing!

But your vulnerability will also prove something else to them…

10) Show them you’ve matured and changed

If you want to reconnect with someone you dated briefly, one of the best ways to do this is by showing them that you’ve matured and changed since you dated.

If you’ve had significant personal growth since you last dated, this can be helpful in reconnecting with an old flame.

If you’ve become more mature, your friend may see that you’re a better match for them now.

You might have had some bad dating habits when you dated them before, but you don’t have those problems now.

You can also show your friend that you’ve matured and changed by listening to their life and experiences.

Don’t focus on what you want to discuss, but instead, make sure to listen to your friend.

Being vulnerable is also a great way to prove your maturity and changes.

If you’re vulnerable, it shows that you don’t have to hide your feelings anymore and you can be open with that person.

You might have hidden your feelings from them before, but now, you can finally be yourself with them.

Revealing your vulnerabilities to someone is a great way to show them how much you trust them.

Final thoughts

Give these tips a try, and you might rekindle things with this person very quickly!

However, understand that some people just aren’t meant to date, so if that’s the case for you two, don’t take it personally.

This says nothing about your worth or your ability to be an amazing partner.

See where things go and just don’t rush anything! You will do an amazing job, I’m sure!

Can a relationship coach help you too?

If you want specific advice on your situation, it can be very helpful to speak to a relationship coach.

I know this from personal experience…

A few months ago, I reached out to Relationship Hero when I was going through a tough patch in my relationship. After being lost in my thoughts for so long, they gave me a unique insight into the dynamics of my relationship and how to get it back on track.

If you haven’t heard of Relationship Hero before, it’s a site where highly trained relationship coaches help people through complicated and difficult love situations.

In just a few minutes you can connect with a certified relationship coach and get tailor-made advice for your situation.

I was blown away by how kind, empathetic, and genuinely helpful my coach was.

Click here to get started.

The above link will give you $50 off your first session - an exclusive offer for Love Connection readers.