Ask Jessica: My Ex Has Reached Out and Wants to Rekindle. What Should I Do?

This month, it’s all about relationships

Ask Jessica is a monthly column in which our resident writer Jessica answers your questions about love, life, and pretty much everything else.  With no subject too embarrassing or taboo, Jessica will tackle the trickiest and strangest of life’s dilemmas with plenty of honesty and life experience. Life is a bumpy and funny thing – sometimes you just need to ask someone for help every now and again!

Dear Jessica,

I’m really struggling because my ex-boyfriend has reached out to me and is wanting to rekindle. The breakup was very sad and I don’t feel like he’s trying hard enough to win me back. What should I do?

Fewer things are more irritating than an ex trying to get in contact with you after a breakup.

All those weeks and months trying to get over the heartache and as soon as they sniff out your closure, they ping over a message that has all the appeal of a mosquito on your arm.

There’s not much clue as to what went wrong here. Either he broke up with you, you broke up with him, or there was some amicable mutual agreement. There are lots of variables here.

If you broke up with him, ask yourself, do you genuinely want to get back together with him? If the breakup was due to him doing something wrong or hurtful, then the answer is most likely (and should be) no. 

Forgiveness should be treated very carefully in relationships because it’s all too easy to treat forgiveness as permission to do something again. Protect yourself first and foremost.

Huda Beauty

If he broke up with you and put you through heartache, then is it worth giving him the time of day? Someone that put you through an emotional turmoil for whatever reason would have to have a good reason to extend a hand to you again and expect you to come back for more. 

When you’re in a relationship for a long time and then suddenly alone, it’s easy to panic. Loneliness can be strong enough to make someone want to throw themselves back into a position of comfort which may be why he’s reaching out to you. But that doesn’t always mean it’s the right thing to do.

All this aside, you don’t actually say that you want to get back together with him or have contact with him, which is a pretty telling sign.

‘I don’t think he’s trying hard enough to win me back’ is a bit of a loaded phrase. What exactly is it you want from him? 

If you want something he cannot give you – to undo something that already happened or fundamentally change who he is – then, honestly, I don’t think you’ll ever really get that.

What’s more, you’re not something to be ‘won’ back. You’re a person with feelings and standards. 

The most important thing here is to think about all the things at stake – your happiness, time, and energy. Is it worth risking all these things on a relationship that has already ended and hurt you once?

If this situation is only going to get more complicated and possibly end in even more sadness, then you shouldn’t engage with him. 

No good will come from starting a dialogue if you don’t feel in your gut 100% certain about rekindling this relationship.

Dear Jessica,

I’ve been going out with my boyfriend for about four months now. I think we’re ready to say I love you, but I’m not sure why he hasn’t said it yet. All my friends in their relationships said I love you to their boyfriends a lot earlier on. Four months seems like quite a long time to not say it, so I’m not sure if he feels the same way. Should I tell him I love him first?

Hey now! Four months isn’t a long time. 

Four months is basically one season. Your relationship is still fresh and new like a little bouncing baby and you should still be in the midst of all the excitement and exploration that comes with getting to know a new love interest. 

That said, if all your friends already reached that stage a lot earlier on then of course you’re going to feel a bit behind. 

But for Christ’s sake, don’t try and force your relationship to match the ones you see your friends having. Relationship landmarks happen differently for everyone.

Some people take much longer to admit their feelings, others might proclaim their love and get engaged after just knowing each other for a few weeks.

There are no rights and wrongs when it comes to timing and landmarks in romantic relationships, as long as everyone is happy and it feels right.

My boyfriend and I said we loved each other around 6 months into our relationship. I wasn’t particularly worried or impatient to hear him say it, because I just already knew in my gut that he did. The verbalisation was just a bonus.

If you feel it deep down that he loves you and you love him, then why worry about rushing to say it out loud?

You write, “I think we’re ready to say…” But this shouldn’t be something you think, it should be something you feel. And it’s definitely not a decision that can be made by one person.

With my first boyfriend, I was so keen to reach that stage of the relationship that I said it first. And he didn’t say it back until I eventually cried about it. …So I guess you could say it didn’t turn out well. 

It’s only in retrospect that I realise that I don’t think it was really genuine love. I just wanted to hear him say it.

This isn’t to try and dissuade you from saying ‘I love you’ to your boyfriend. I just want you to be sure that A) you actually do love him and B) you’re sure he’s ready to say it back. 

Because saying you love someone and not having them say it back is about as soul-crushing as it gets and you will spend the rest of the relationship wondering if they actually mean it.

I see no reason why you shouldn’t say ‘I love you’ first. After all, this is the 21st century. But to be honest? It doesn’t sound like you should just yet. 

If you ‘think’ you’re ready to say it purely by comparison to your friends and if you’re not sure if he’s ready, then it sounds like it’s being forced.

Relationships should be less about thinking and more about feeling. When you’re sure that you’re both ready, don’t just say it for the sake of saying it – say it because you mean it.

In last month’s Ask Jessica, it was all about friendships.

Tags: advice, Ask Jessica, boyfriend, relationships

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Jessica Cullen
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I'm an avid lover of film and television. I'm also a true crime obsessive and I swear by the three F's: flea markets, frozen margaritas, and Fleetwood Mac. When I'm not writing, I'm posting pages of my embarrassing childhood diaries on my newsletter The Jessica Diaries.
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