Ask a Guy: When Can I Ask About His Past Relationships? post image

Ask a Guy: When Can I Ask About His Past Relationships?

I dated a guy for two months and everything seemed perfect until he told me that his last relationship was three months ago. That relationship was a year long, so when he started seeing me they had only been broken up a month. Once that was out in the open he started distancing himself and I eventually broke it off because I was over the inconsistency.

I typically don’t like bringing up the past. I feel like the past should be left alone. But after my last experience I think it’s an important thing to know so that I don’t put myself at risk and end up the rebound girl.

So when you should ask a guy when his last relationship/serious dating/fling was? And how can you do it without it coming off in a negative way?

How recent his last relationship was isn’t a problem in and of itself.

His relationship with you is what it is… your relationship isn’t a thing (like a stone or purse or car).

A relationship is like music: it is what it is as it’s being experienced. In the same way, a song on your iPod isn’t the music… you hearing and experiencing the song in the moment of listening and feeling it as it pulses through you and spreads through your body, pounding through your consciousness… that is the music. And that is your relationship. You feel your experience of the relationship as the music is playing.

When you’re with a truly compatible person, you can feel that happiness in the center of you… you can feel it spreading through you… you can feel the joy of wanting their presence, loving their existence, and their way of being.

In that way, I can’t imagine that your relationship (and his presence in your life) felt that way…

Sure, I can imagine that you might have felt your relationship with him was very significant, important, urgent, etc. But I can’t imagine that you weren’t simultaneously feeling a growing sense that something was wrong when you were with him… that something wasn’t quite right. I don’t know exactly what you felt, but whatever it was, I know it didn’t feel good.

Maybe it felt like worries… or paranoia… or resentment… or insecurity… or anger… or a feeling that you weren’t enough or worthy of him… or something else that just didn’t feel completely and purely good.

And this is one of the most confusing parts of our journey towards finding pure, true, complete love: We must learn the difference between being intoxicated by a relationship with another person and being truly happy with another person.

MORE: Is It True Love or Unhealthy Obsession?

What does it mean to be intoxicated by another person?

It feels like your relationship is spiked with a kind of poison. You feel this urgent, suffocating, disturbing kind of feeling when you’re with them… and it usually gets worse and worse as the relationship goes on. But it also feels like you have to win over that feeling… defeat it… destroy it… find a way to finally “solve it” so that you can have the relationship and have peace… relief…

This creates a sort of emotional roller-coaster effect, which is the heart of emotional intoxication. When they do or say something that allows you to stop thinking or feeling the negative thoughts you were having, the ending of that negative feeling brings you tremendous relief.

And here’s the most important thing to understand: We misinterpret the feeling of relief that comes with the ending of the negative feelings as the relationship giving us a good feeling, when really we’re only feeling it because the relationship normally feels so bad.

We don’t realize it, but choosing to be in an intoxicating relationship is about as silly as intentionally wearing extremely tight and uncomfortable shoes for hours only to get the “pleasure” that comes with taking them off.

When we don’t see this, we unknowingly end up in relationships that become the greatest sources of misery in our lives.

MORE: Rules to Live by to Get the Relationship You Want

Even when we do realize this, cutting off a toxic relationship can feel like we’re giving up or “losing.” And so, even though we’re miserable… even though our minds are screaming at us that we’re on the wrong path… we mistakenly believe that dropping the poison is a loss or would make us less, when really, it would finally give us the peace, joy, and fulfillment that we’ve been trying to get (but have felt like we could never quite reach, because the poison we’re subjecting ourselves to is the cause of the lack of joy, peace and fulfillment… not the path to get to it).

The point is, it doesn’t matter when his last relationship was or when you bring it up. If it’s a good relationship, it will work. If it’s a bad relationship, it won’t…or it will be incredibly unpleasant and stressful for a while and then it will come apart.

If two people are in a good place in their lives and can bring that into the relationship, there’s nothing to worry about and no issue that needs to be solved. You’ll be able to trust what you have and won’t be bothered by what he had before you. It’s all about being in the right place internally and putting your focus on managing your mood and your happiness, not figuring out the right time to ask him a certain thing.

Hope this helps,

eric charles



Written by Eric Charles

I'm Eric Charles, the co-founder and co-editor of A New Mode. I love writing articles to help people free themselves from suffering and have clarity in their love life. I have a degree in Psychology and I've dedicated the last 20 years of my life to learning everything I can about human psychology and sharing what gets people out of struggling with life and into having the life they really want. If you want to contact me, feel free to reach out on Facebook or Twitter.

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I can see why some find this post helpful but honestly the OP’s question was never answered and her question was when should you ask about past relationships? I have an inkling that the OP would’ve never put as much time and effort into dating this guy had she known that he had recently broken up with his ex-girlfriend, obviously there are numerous reasons why anybody does not want to date somebody fresh out of a relationship. And her question was when should you ask about past relationships? I have an inkling that the OP would’ve never put as much time and effort into dating this guy had she known that he was recently had recently broken up with his ex-girlfriend, obviously there’s a number, numerous reasons why anybody does not want to date somebody fresh out of a relationship

Reply April 11, 2017, 6:13 pm


Thank you Eric for this article. You are right, it’s not how recent the last relationship was, as in, how much TIME it might take to “get over” someone, but more importantly, what that relationship did to them…was it a good or bad break up? Was it getting out of a toxic one or being the toxic one in the relationship and the other partner broke it off?

Also, what you said about the past not really mattering if the relationship you have is a healthy one is very true…Recently, I had to tell my boyfriend who is a very nice and honorable man, but has never been well off, that my first boyfriend is a very famous rock n roll star. He was able to accept it very well because our relationship is a healthy one…he understood that what I was really saying is that I am with him because I choose to be with him and the reason I am divulging my past relationships, or at least this one, is to ensure he wouldn’t be blindsided by someone mentioning my famous ex and not because I was trying to make him feel inferior or even to manipulate him in some way.

Reply August 19, 2015, 4:06 pm


I am always good at giving the perfect advice but when it comes to my own relationships I can never see the actual picture and don’t know what to do. My boyfriend broke up with me because he said he doesn’t trust me. I have never cheated on him and I don’t even flirt with other guys. I do have guys approach me all the time even when I am with him though and he gets mad at me about it. I even had my ex (guy I dated before him) approached me at the bar in front of him just to tell me he was sorry for treating me badly and told me he was moving out of the country, I told him I was there with my boyfriend and had to go. So I only talked to him for about 5-8 minutes. But my boyfriend (who is now my ex) got super mad about it and said he thinks since I gave him the time of day that I have feelings for him. I don’t at all, I just felt like it was the adult thing to do to let the other guy apologize. He would get mad if a guy texted me, and he even went through my phone when I was sleeping and got super upset about there being old texts in my phone from an ex even though the texts were before I even knew him. Anyway, the relationship was perfect but he became more and more paranoid and jealous. Broke up with me because he says his gut feeling tells him he can’t trust me. I still love him. It has been a month and we haven’t spoke. But he checks my social media and snapchat every single day. What does this mean? Should I move on? Or does he just want space for a while to figure things out but still misses me? I did send him one text a few weeks after we broke up and I said “i miss you” and he never responded. I just want the harsh truth if I should move on or wait for him to contact me.

Reply February 1, 2015, 11:28 pm


There was a guy I worked with several years ago and we connected right away. Timing was never good for us and after a few false starts we decided to let go and move on. We’ve been friends since we met and still talk all the time. Within the last year or so I realized I never really got over him. We were texting the one night and he admitted that he and his girlfriend had somewhat recently broken up and he was playing the field as he had always gone from one relationship to the next. I got the courage to ask him out and he said yes as long as I realized he was dating a couple other girls too and was ok with it. I consider myself to being pretty laid back and as I myself was dating someone of course I was fine with it.
That was this past fall. He is still single but hasn’t been dating anyone. We only had the one date as we could never sync our schedules. A few days ago I sent him a text basically asking him out again and that I wasn’t sure how he felt about me but I didn’t want to make him uncomfortable if he didn’t feel that way about me. His reply had been that he didn’t want to talk about it through text and wanted to talk in person. I assume that means he doesn’t feel the same? If he doesn’t I can handle it and I know he knows that but why is he making me wait to tell me?

Reply January 27, 2015, 4:31 pm


I have been getting a lot of the tell-tale signs that a guy likes you, and I’ve been giving him signs too, but he keeps saying he just wants to be friends. As in today he said this, “I just want to be friends, for now, at least.” and this wasn’t alone we were in a semi crowded place, but also just the day before someone said how we should date and he said, “Yeah we should.” I’m just really confused on how he really feels towards me and I would like some answers to explain his actions.

Reply January 22, 2015, 3:51 pm


what do i do i love my best friend he says he loves me and wants to be with me but he said he also still loves his ex i think he always will because i think she was his 1st love or something she has a boyfriend now but tells him she still loves him and wants him what do i do. And i kbow i shouldnt of let him probably keep things the way they were but hes not officially my boyfriend its complicated. What should i do we keep giving space saying if its ment to be it will happen and everytime we keep coming back to eachother. What should i do????

Reply January 13, 2015, 10:03 am


When is saying “I love you” way too soon? Within the first week of seeing this very sweet and what I feel like is the beginning of something absolutely beautiful…he told me that he loved me. For a couple days I could tell when he looked at me that he was reserved about coming out and saying it but he eventually just did and said he wasn’t going to apologize but that’s how he felt. My kids are away with their father for the holidays so we’ve been spending almost every moment with each other for the past 27 days…and I couldn’t be happier. However, I wonder if this isn’t right even though it feels right. Am I being ridiculous?

Reply December 28, 2014, 7:17 pm


If the feeling is mutual, you can relax..

Reply January 19, 2015, 12:53 am


Great article and perfect timing may I add……what happens when it’s the other way round? I accept his past but im not sure he can accept mine. I never lied about it only (with reason, withheld name) im entirely curious to the reversed answer

Reply December 26, 2014, 4:57 pm


hi everyone
i need help from everyone who is reading this
my girlfriend mind is unstable toward me i tried to ask her what’s the reason she replied that suddenly i don’t have any feelings for u,and i don’t want to hurt u in future by ditching u because i am confused between you and my close friend whom i have feeling similar like u
and i have courier tension also..
she knows how much i love her i had cried also i m depressed too much due to her behavior she needs only friendship with me and not more than that but i am afraid of losing her i love her lot every moment is killing me without her…
i am confused what should i do i really dont want to lose her i lover her lot….
please help me…

Reply December 24, 2014, 11:28 pm


What is a guys perspective if your holding back on inter course but having oral sex? Is it the same thing?

Reply December 22, 2014, 11:47 am


Lol! Ofcourse it’s the same thing 0_0

Reply January 19, 2015, 12:55 am


I’m in a relationship this is our third year dating wirh this guy,I love him but the problem is distance he is working in Cape town and he even introduced me to his family so does that mean he loves me and even having further plans with me?

Reply December 15, 2014, 12:09 am

Candace Casingal

Hi! Can I ask for some advice about this? I’m seeing this guy twice. We had a great night. We watched stars and get to know each other. It bothers me when he told me “he’s with a friend named Maria”. I felt jealous. Yet, I told him but after that he didn’t reply anymore. ahmm! do i have the right to be jealous and why he didn’t texted me anymore? I’m waiting for his text until now.

Reply December 13, 2014, 12:28 pm

Alexander lavruk

A lot of times people jump in to a conclusions with out doing enough research. If you are looking to be part of his life and make him your MAN, then you should be ok with any friends that he has because you should already assume that he is your MAN and all others are just friends. Its important to find out there relationship before being jealous. At the end of the day your task is to get to know him and that includes his circle of friends. My suggestion is to be excited about getting to know his friends, females, males etc. And only when you see there dynamic first hand, make conclusions. The biggest issue relationships have is creating a problem with out knowing all of the facts. Chances are you expressing to him how you feel, made him yet again make wrong assumptions about who are you truly. Im not sure what have happened since that day but try to reintroduce yourself to him and treat him as a new person, at first as a friend. Approach him with mentality of a friend who is actually curious to meet his friends but only if he feels comfortable sharing them with you. IF he is being weird about introducing you to his circle and especially Maria then he might be hiding something from you as far as his relationship with her. But thats a whole new story. Over all, do your research, first hand research before assuming and explaining how you feel. This way you would have a lot more backing behind your emotions.

Reply December 16, 2014, 7:32 am

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