Your Ex-Girlfriend Wants Your Help. What Now?

Every so often you’ll get an ex-girlfriend reaching out to ask you for help. This is common in the first ~6 months after you guys break up.

When the breakup is still fresh, the new norms are often not yet established over what is allowed and what is not.

But, it can happen years later.

But should you help your ex?

As with all relationships, context matters.

There are several situations where it makes sense to help your ex-girlfriend, if certain conditions are met. However, there are oodles of cases where it doesn’t make sense. Which bucket does your situation fall into? Let’s find out.

Why Does Your Ex-Girlfriend ACTUALLY Want Your Help?

There are generally 4 reasons why your ex-girlfriend wants your help.

You haven’t set a firm boundary with her;
She still trusts you;
You owe her a debt (real or imagined);
She wants to keep you on the hook as a backup plan;

Let’s briefly dive into each.

1: You Haven’t Set A Firm Boundary With Her

Look – I get it.

Boundaries are fucking diabolical – especially when you’re grieving the loss of the woman who was supposed to love you.

And now you’re somehow supposed to navigate this new normal of “drawing the line” with someone who’s wrapped up in a confusing bundle of hurt, anger, disappointment, guilt, and regret.

It’s fucking hard. I don’t blame you if you are struggling to draw a red line in the sand.

Who’s to say what’s fair or not?

Or perhaps you’re afraid that sticking up for yourself – because you believe that growing a fucking backbone and allowing your basic instinct for self-preservation to take over – may somehow push her further away.

And you can’t stomach that thought of losing her, can you?

So you roll over when she asks you to do something that leaves you questioning.

Either way.

I don’t blame you.

But here’s the hard lesson: there are people (men and women both) who will continue to take, and take some more from you – until you put up the hard boundary that says “I respect myself, and I will not continue to be taken advantage of”.

Some people know that boundary exists and will possess enough emotional intelligence not to test it. Some will know, but try anyway – for lack of a better term, to fuck around and find out. But there are others who either lack the emotional intelligence to recognize an inappropriate request, while there are still others (read: narcissists, sociopaths and the like) who don’t give a shit about your boundaries at all.

While I’m not here to diagnose the woman asking you for a favor – you should take a long, hard look in the mirror.

Is she asking for help because you haven’t stood up for yourself? Is it because you have trouble saying no?

Is it because somewhere, deep down in your heart – you believe that respect, friendship…and even love are earned by a reciprocal balance of favors that constantly hangs over your head?

Look in your heart. You’ll know the answer.

2: She Still Trusts You

If your relationship ended on relatively loving, and trusting terms – and now she’s randomly come out of the woodwork with a request, there’s a good chance that what she’s going to ask of you is either:

Something that she believes you can only trust you with
Something that only you can understand

We’re talking about things like: family issues, self-esteem issues, friend issues and similar topics. Usually these are problems that you know she wouldn’t feel comfortable talking to other people about.

Sometimes – this favor is in a work domain. I’ve seen it more than once where an ex-girlfriend comes out of the woodwork to ask for career advice, guidance, or a recommendation.

I worked with a client not too long ago who was a great example of this.

My client was dumped after he decided to pursue a career opportunity that his ex-girlfriend was not in favor of. She didn’t want to move and leave behind her family. Understandable. The relationship ended on good terms.

A year and a half later, she was in his new city and she reached out, asking for job advice at the company my client had previously worked for. It was a relatively tight-knit industry. My client met her for coffee. Over the course of 4 months, a few “work favors” turned into her showing up as his new apartment with a “thank you” bottle of wine.

You can guess what happened next.

It’s possible she doesn’t have many close relationships with her family, social, or professional circles. It’s also possible that you still stand above them in the specific area where she needs a favor from you.

To certain people – history, being there, and being reliable counts – even years after the fact. This is often the case with those who aren’t very outgoing, or who come from tough backgrounds. Once the trust is build – and for lack of a better term “she lets you in” so to speak, you’re in.

And once you’re in, you’re on the helpline speed dial.

The upside here – is if she still trusts you, she may be open to getting back together.

Because the age old social contract is true – asking for a favor can be a weak position to be in, one that implies a debt of gratitude towards you, and the awareness that the favor should be given in kind.

3: You Owe Her A Debt (Real Or Imagined)

It’s possible your ex-girlfriend believes you owe her something because of something she did for you during the relationship. It’s possible that her request for help is a way to collect on that debt. This is often the case for past financial troubles, especially if she supported you for a time or has lent you money in the past.

She may not be upfront about her request for help being a way to collect on a debt. Other times, not so much. Use your best judgment here. If she was an extreme “50/50” person during the relationship, or is used to getting her way this may be the case.

Alternatively – if she was altruistic and didn’t keep score – or was a forgive and forget type of person, it’s less likely that her request for help comes from a place of getting “what’s owed” to her.

It’s important to approach the situation with caution and be clear about your own boundaries. We’ll get to this in just a minute.

You don’t want to feel like you’re being taken advantage of, but at the same time, you may want to consider the possibility that there is some validity to your ex-girlfriend’s request.

Ultimately, the decision to fulfill the favor should be based on what feels right for you, and not on any sense of obligation or guilt.

4: She Wants To Keep You On The Hook

If you look at her request for help and find yourself thinking:

“What the fuck, she could have asked anyone for this”

Then chances are – her request for help is not what you think it is.

Your ex-girlfriend may use a request for a favor as a way to keep you on the hook as a backup plan by leading you to believe that there’s still a chance for the two of you to get back together. She might use the favor as a way to stay connected to you, to test the waters and gauge your interest in her, or to create a sense of indebtedness that could be leveraged in the future – to reach out and “make amends”.

These are usually stupid requests, ranging from interview prep, all the way up to asking for advice on current relationship prospects.

Ultimately, she’s not doing it because it’s devious, she’s doing it because it works.

I worked with a client in the past who’s ex-girlfriend would ask to come by to do her laundry – and they would end up having sex. This went on for several weeks, until one day she stopped coming by. The reason why? She started dating someone new.

I’m not saying this is always the case, but keep your eyes open.

Helping her out will also tell her that she’s got you on the hook, and she can reliably count on you as a backup plan should her current romantic endeavors fail.

Ultimately, it’s a really low risk way for her to get what she wants, and she knows that.

Alright – now that we’ve covered the 4 reasons, let’s dive into some practical applications.

Should I Help My Ex-Girlfriend Financially?

It feels like every day I’ll get an email saying something like “Jack, my ex-girlfriend is asking me for money” or “Jack, my ex-girlfriend wants to borrow money – what should I do?”

My answer?

It depends.

First, let’s talk about lending your ex-girlfriend money.

Under No Circumstances Should You Let Your Ex-Girlfriend Borrow Money

Don’t fucking do it man. You’ll regret lending her the money, I fucking promise you.

If you’re serious about living a life of long-term, masculine happiness – lending money to friends and family is a bad business to be in, even if they are the most responsible human being in the world.

When you lend money to your ex-girlfriend (or any friend/relationship, really) you create an unhealthy dynamic that can damage your relationship further. Even worse, it can give your ex-girlfriend an incentive to avoid you even further, which you may not want, especially if you’re still trying to get her back.

Even if you aren’t, it’s likely that you still have some type of relationship with her – whether it’s a friendship, respect, or even love for. Do you really want to damage that love over some money?

I sure as hell don’t, and I don’t think you want to either.

TLDR: Don’t lend your ex-girlfriend money under any circumstances. Think twice about doing it for friends and family too.

Okay, now that we have that out of the way.

Notice I didn’t say anything about giving your ex-girlfriend money?

Giving Your Ex-Girlfriend Money With No Expectation Of Repayment Can Be Okay

Giving your ex-girlfriend money is a lot different than lending her money.

This is where it becomes a judgment call.

First, you want to consider your objectives.

Because you’re reading this article, I know at least 1 of 2 things is likely true:

You want to get back together with her OR maintain some kind of amicable relationship / friendship
You’re still not fully over the breakup yet and this favor request is making you feel weird, uncomfortable, and indecisive

Heck – it might even be both!

So here’s the rub – if the idea of giving her money makes you feel weird, uncomfortable, or indecisive – don’t give her money.

Simple as that.

When you feel uncomfortable with a request like this, it’s often a sign that you have an expectation or a boundary that you feel is being disrespected.

Put yourself in her shoes. Would you ever ask her for money?

If the answer is a resounding “hell no” – then don’t give her the money.

The one exception to that is if you have children together – but more on that in a minute.

But what about if you are comfortable giving her the money, and you want to get back together with her or maintain an amicable relationship?

Then it depends on the context of the request.

Again – this assumes that you are flush with cash and comfortable giving freely, which means with no strings attached, no promises of repayment, or expectation that your relationship with her will improve.

You’re better off saying no if:

This is not the first time she has asked for money. Unless you share a child/children, you’re likely subsidizing poor lifestyle choices or her drug habit.
She won’t give you a straight answer about what the money’s for. She might spend it on something she really doesn’t need – like a vacation, drugs, school expenses, etc.
She had financial issues during the relationship. Perhaps you were the saver, she was the spender. This pattern is likely still the case. Bailing her out gives her no incentive to change.
She’s trying to make you feel guilty. Anyone that uses guilt as a lever to get you to conform is not someone you want in your life.

On the other hand, there are some situations where it makes sense to say yes.

You have children together. This is a topic in and of itself – but if your ex-girlfriend wants money to do something for your child/children and you have the money, you should give it to her. Kids come first. The longer answer to this involves a parenting plan with clearly defined boundaries – but that’s a topic for another time.
She was generous during the relationship. If she took care of you and was otherwise good, supportive, and always willing to give to you (not just money) – then it can make sense to keep the spirit of social exchange going.
She’s in a rough spot. Whether that’s medical bills, housing issues, etc. I know it’s tempting to be vengeful and say “fuck that bitch” because she hurt you. But on the other hand, long-term masculine happiness is about rising beyond petty grievances. Plus – generosity makes you happy.

Should You Give Your Ex Relationship Advice?

You should only consider giving your ex-girlfriend relationship advice if:

You’re completely over the relationship;
You’re still friends;

If neither of these apply, resist the urge to give her relationship advice if she asks for it. Not just because it’s no good for you (because it isn’t, and I’m sure you know why) but because the advice you give her is likely to be jaded and tinged.

Are you really at the point where you can objectively help her?

Yes, you can offer her a valuable perspective – likely better than just about anyone else when it comes to relationship advice. You’ve seen her good and bad, her strengths and faults.

But you’re not her therapist.

You’re not her relationship coach.

And unless you’ve moved past the relationship and you’re able to let go of any desire other than to see her happy, I’d stay away from giving your ex relationship advice.

Should I Keep Helping My Ex?

In the past, I used to answer this question as a hard no in all circumstances. However age, experience, and working with hundreds of different clients has changed my mind.

While I can’t give you an exact answer without more information, here’s a really simple protocol to answer whether or not you should keep helping your ex – which works whether you want her back or not.

If you answer “yes” to any of these questions, you should decline her request for help.

Do you have a valid reason to feel angry, uncomfortable, or upset by her request?
Did you struggle with boundaries in the relationship, or in the past?
Is her request for help outside your ability to reasonably provide?
Has she refused to show good faith when you’ve needed her?

Tell her “Hey [insert name] I don’t feel comfortable helping you with this” and leave it at that. You don’t owe her an explanation. If she gets mad at you, realize that it’s likely that she’s pissed that she’s not getting what she wants, and not a reflection on you being a shitty person.

Look, it’s hard enough putting your life back together after you’ve had your heart broken. Doing so while trying to be selfless around the person who your grief is wrapped up in is even harder. It can lead to resentment, anger – and in the worst cases it can even destroy your self-esteem.

After a relationship ends, you owe her nothing. Especially if she chose to break up with you. What does it say about you as a self-respecting man if you continue to bend over backwards for her – or even worse, violate your own standards of conduct just to please her?

Part of getting her back, is establishing yourself as a guided and focused man who doesn’t have time for bullshit.

So keep your eyes open.

TLDR: It Fucking Depends Man, Think About It

If your ex has a LEGITIMATE need of a favor, handle it quickly. Don’t use it as an excuse to start talking with her. Robotically address the logistics and go back to no-contact.

Again, we’re prioritizing YOU and YOUR emotional recovery. Not her needs.

Take your time man, there’s no rush.

Talk soon my friend,

Coach Jack

PS: Got a burning question about your ex-girlfriend or your unique situation that you want my expert advice on? Click here to learn how I can help you.