The following article is based on an edited transcript of the above video:

Dear Harry,

I recently found myself in a particular situation just a month and a half ago. I got engaged to my now ex-fiancée. But we had to part ways due to our inability to find common ground and resolve our differences.

Well, I’m sorry you’re going through that, but these are the kind of conversations that you should have been having with this woman way early in the dating process, like on those first few dates where you get to learn the ins and outs of what they like, what they don’t like, and where you two are gonna be compatible and where you two disagree. Because some of those things that you disagree on could be things that end up being deal breakers in the long term.

I think, for a lot of guys, they’re just so happy to get on dates that they figure, “Well, whatever kind of thing I run up against, it’s no big deal. I’ll be able to either fix that for her so she agrees with me or I’ll be able to eventually deal with it.” And sometimes, those deal breakers that you think you’re gonna get by are not gonna be things you can get by. So you have to do your job early on and know that there are some things that are just not gonna jive with you.

That means that you, unfortunately, are going to have to say, “I can’t continue to date this person, even if I find them extremely hot, even if we had a good makeout session, even if we got the hookup in her apartment or my apartment, it felt good.” You can’t let those things deter you away from your ultimate goal, which is to find somebody that connects with you in various ways that are going to be agreeable to you and your lifestyle.

However, before my engagement, an old crush from years ago unexpectedly reached out to me, expressing her interest in being more than just friends. At the time, I chose to pursue my engagement and never acted upon the opportunity with my crush. Now that I am single again after a six-year relationship with my ex-fiancée and my crush has also ended her eight-year relationship, I can’t help but wonder when would be the appropriate time to explore the possibility of being with my longtime crush.

She reached out to you while you were still in a relationship; she probably didn’t know at the time when she reached out that you were still in a relationship. But my question is, at the time that she reached out to you, was she still in the relationship with a previous guy, or had she ended that relationship and then reached out to you?

If she reached out to you while she was still in the eight-year-long relationship, then I would say, don’t even pursue this anymore. Because at this point, she was trying to monkey branch, meaning she was trying to see if another relationship was possible while she was still in a current relationship. And even though that is a tactic that women often do, it should not be one that you accept because then when you get into a relationship with her, there’s a chance that she could also try to monkey branch over to somebody else if you two get into some kind of tiff or disagreement.

But I’m going to assume for the situation that she was with the guy for eight years, and then at some point, she reached out after their break up. I’d be curious to know what her timeline was. Like, from the moment that she broke up or their relationship with her previous guy ended to when she reached out to you, what timeframe was there in between that? That would be something that I would want to figure out, just because I’m nosy and I’m curious to see what that looked like for her.

Now, on your end of things, here’s what I believe, guy. I believe that we are made to think that if we’re in a long-term relationship with somebody else, we should have months or even years of time that we have to spend trying to get over them at the point that the relationship is over. And I don’t fundamentally believe that.

Here’s why: let’s say you were a woman, right? At the point where they break up with you, most guys think it’s all of a sudden just happening to them because it usually is. But most women, at the point where they start thinking about a breakup, it’s usually about six months before they actually do it.

What will happen is they’ll start getting that feeling of: “maybe he’s the guy or maybe he’s not the guy that I now see myself with. But you know what? I don’t want to trust my feeling right now. I want to really give this time to see if it builds back to where I had the feelings that I had for him before that were really high, going in the toilet.”

So a woman will give herself three to six months with you from the time that she thought about breaking up with you, just to make sure that’s really the decision. Because women know that if this is a breakup, there’s a chance that you’re not going to want her back, and she’s not going to want you back. And I say this because it’s important to note that women are typically starting to get over you while they’re still in a relationship.

So at the point that a woman breaks up with you, she can usually take two or three weeks to sit with herself and cry about it and feel bad. And then be right back out there. Because it’s not that she broke up with you and it’s only been three weeks. In her head, it’s been three weeks in addition to the six months she was already thinking about getting rid of you.

So, I said this to say: if you are a guy that has emotional intelligence and is able to say to yourself, “You know what, as much as I wanted this to work, the reality is she can want what she wants, and she’s welcome to go get that. And I’m happy for her. And I have a right to get what I want and be able to pursue that however I want to,” you could break up with a woman on day one and by day two or three, be going out with somebody else.

Now, obviously, if the woman that you’re pursuing is aware that you’ve just broken up with somebody, then they might have some questions about how devoted you’re going to be to them and if you had enough time to get over that situation. This is fair because if you go through a breakup and then you go out the next night and hook up with somebody and try to start a relationship, you really haven’t dealt fully with the emotional baggage from the previous relationship that might’ve caused it to end.

At the point where you feel as though you’ve been able to sit with yourself and go through the thoughts about what worked in the last relationship and what didn’t work, and how you could have shown up better, and then actually done a bit of work to try to see how you can balance out those things so you show up in the next relationship better – that’s when I feel it’s fine for you to go out and start dating again.

Now, if you’re a guy who is anxious about dating and is very, very pushy, then that could take you a bit of time to get over the ex, to cry about her, and to tell your guy friends about how much of a B she was or how much you messed up, or whatever. That could take you months on end because you’re heavily attached to the outcome of everybody you date.

If you’re a guy like me, whereby you could date somebody for a year, two years, three years, and it suddenly breaks up, I’ve done enough self-work to where I can legitimately sit with myself for like a couple of weeks or a couple of months and really have time to think about that relationship and really analyze where it went wrong. But in terms of me being heavily attached to that person still, I don’t typically have those kinds of things happen because I’m very indifferent to dating and outcomes and stuff like that to where I could realistically go out with somebody after like a month or so, you know?

So you have to determine where you’re at though with that because some guys really need to sit there and do the work and mull over their ex and stuff like that. And I know some guys think like, “Well, I was with this girl for six years, so shouldn’t I be grieving her for like six months?”

I don’t believe that’s a thing. I think that you grieve in the best process for you and however long that takes. But you don’t have to grieve for a certain amount of time to make your ex feel good or to make the new person you’re dating feel good. Like I know a lot of people think, “What if my ex finds out that I dated somebody two weeks after we broke up?” It doesn’t matter if you dated a year after because she’s no longer in the picture. Ideally, you don’t have contact with her anymore. You’re not trying to show off on social media that you got a whole bunch of new dates. So you just need to move on and focus on your own healing process.

You also no longer have to care about her thoughts and feelings in this process because as far as you know, this is officially over. She’s no longer in your life, and you can move on to bigger and better things. So what that process looks like for you may vary. If you’re asking if there needs to be a specific timeframe, I don’t believe in that. I believe that depending on who you are, you might be able to get over somebody in a span of like a week or two and go back to dating. Or you might be a guy that needs six months.

Either way, I’m saying, whatever you feel your timeline is, don’t think that you have to be rigid in terms of what a specific timeframe has to look like. Because you might be thinking today, “Man, we broke up. I’m gonna be distraught and devastated.” And then next week you go to a party and you meet a hot girl, or in this case, you have a crush from years ago who reached out to you and said, “Hey, I want to go out.” And you were at the time in a relationship, but now you’re a free agent.

So if this girl knows that you were in a relationship and you were engaged, you might wait a month and then just say, “Hey, I was thinking we can meet up for like lunch or something like that.” And then during the course of that meeting, you could say, “Hey, so just want you to know that me and so-and-so broke up.” And then you could tell her, “You know, right now, I’m just kind of like, eh, I’m not rushing to get into anything, but I would like to meet up with you some more and maybe hang out.”

Because you can realistically say to another person, “I’m not fully ready to dive into something yet. I’m not sure if I want to now go down the pathway of seeing what this looks like, but I want to start spending time in the event that I start to feel those things.” Because you already felt something for her in the past, and so you don’t have to – obviously, you didn’t break up to try to get with this woman – but you can say it just didn’t work out with the previous person, and now you’re just out there trying to see what’s what.

You can say, “I’d love to hang out and take you out and see where that goes.” Like, you’re not trying to pressure her into saying, “Now that I used to have a crush on you, and you used to have a crush on me, we should automatically go out.” You’re not gonna say that because what I don’t want you to do is go back to her and say, “I’m a free agent now, so let’s go out and be boyfriend and girlfriend.” She’s gonna think this is too fast of a process.

But you can realistically say, “So why don’t we just take things a day at a time? I’ll hit you up sometime, and we can go out and just see what’s what, no pressure. Obviously, we liked each other before, so we can just hang out and maybe see if that spark is still there. If not, it’s no big deal. But if it is, that would also be awesome.” And that’s how I would say is your best way to handle the situation. But don’t get hung up on having to wait X amount of time before you see somebody else type of thing. That shouldn’t be a thing in your head.

Got a question for Harry? Write me at [email protected]

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