I am 18.

I don't know why but I feel like I am competing with my ex-girlfriend (lets call her X) who dumped me around 2 years ago. It was the first relationship for both of us and I was very emotionally attached to her. Since we broke up I hit a slump in my life and entered a depression phase for 6 months or so. I then felt I had moved on, and decided to start dating again. After that I went on to date 3 people. I never felt the same spark and always thought the relationship wouldn't work out. I ended all three of those relationships.

I have now finally met a girl I like (lets call her Y). I took it slow this time and really got to know her before getting into a relationship.

Now about the competition bit: X got into an Ivy League College.

For some reason I feel insecure about this and correlate it with me holding her back. To somehow prove her (more like my own assumption) wrong, I have started studying very hard and trying to achieve as much as I can. I do enjoy the productivity. But I hate the motive. I want to discuss this with Y and try to overcome this insecurity.

However, the 3 girls I dated in between all pointed out that it was very irritating when I spoke about X. It also hurt them in many ways and destroyed the chance of the relationships working. I do not want this to happen with Y. I do not want her to think I am not over X and yet be able to discuss my past.

How do I open a discussion about this topic without making my current girlfriend insecure about our relationship?

  • 1
    Well, note that this site is not really intended to help with what you should do, but rather with how you communicate your decisions to the other people (I was told, someone may correct me). The middle passage of the post seems to show that you compete with X and compare yourself to X. Is this assumption right?
    – yo'
    Feb 20, 2018 at 16:30
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    If X didnt went to Ivy League College would took that road anyway? If you can answer that question you can plan your action more easily. Feb 20, 2018 at 19:09
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    Please don’t write answers in comments. It bypasses our quality measures by not having voting (both up and down) available on comments, as well as having other problems detailed on meta. Comments are for clarifying and improving the question; please don’t use them for other purposes.
    – Mithical
    Feb 21, 2018 at 9:14
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    Why do you want to discuss it with her? and how would you feel if she started discussing an ex boyfriend with you? Not saying you're wrong but this can help us see your motivations.
    – FreeElk
    Feb 21, 2018 at 11:49
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    What is the pivotal point: a) X got into Ivy League, and X is your ex, so you'd need too, or b) someone you knew (let's call this person X) got into Ivy League, and seeing how it worked for them, you might try, too. So, how important is X being your ex in the equation. Because that's the rather issue that bodes with the now-girlfriend not well. Not that you chase a certain person from the previous segment of your life, but that this certain person was your ex. (Not an answer, 'cause no suggestion how to communicate the issue.) Feb 21, 2018 at 17:23

4 Answers 4


This is, perhaps, not a conversation you should be having with your new girlfriend. Sure, she should be the one person you can discuss anything with, and lean on for support, but it's still a fairly new relationship, and no one is going to enjoy hearing that you constantly compare your situation (and therefore your current relationship) with that of your ex.

Instead, I would focus on your own well-being. Get your house in order, and then reveal your struggle and insecurities to your partner as something that you're tackling head on, and she need not fear.

It sounds like you put all your eggs in one basket as far as your former relationship was concerned, and that it left you quite broken when it didn't work out. The problem is that you allowed yourself to be defined in terms of your relationship, not in terms of your own personal achievements as an individual.

And you're largely still allowing yourself to be defined in terms of your ex, and her achievements. You need to come to terms with the fact that things did not work out, and desire success not because you want to spite her, but because you genuinely wish to better yourself.

I would sit down, get a piece of paper, and write down:

  • Your successes, and skills you've developed so far in life

    e.g. I can play the guitar quite well; I get B+ averages, etc.

  • The list of personal traits that you are proud of

    e.g. I am fit / have a good diet; I am an analytical thinker; I am open minded; etc.

  • A list of things you'd like to improve on (essentially, short term goals)

    e.g. I'd like to learn to play X song on the guitar, which is currently beyond me; I'm overweight, I'd like to lose 30 lbs; I'd like to improve my grades to an A average, etc.

  • Develop a concrete plan on how to achieve those short term goals

    e.g. I will practice guitar for 30 minutes, 3 times a week; I will study math 30 minutes a night, every night because that's my lowest grade, and it will bring my overall average up; I will work out for 30 minutes every day, come hell or high water; etc.)

  • Set a long term goal (such as getting into an Ivy league college), and see whether your short term goals are aligned with your long term goal

    e.g. I want to play basketball at least 2 hours every week, but my grades are not good enough to get me into [School Here]. Perhaps those 2 hours would be better spent studying; etc.

The point of this exercise is to figure out the things about yourself that you can be proud of, and to redefine your goals in terms of the things which interest you, and you wish to accomplish.

It would probably also be a good idea to completely cut your ex out of your life. Block her on social media, delete her number, etc. Cut off all contact.

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    come hell or high water what those mean? Feb 20, 2018 at 19:05
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    @JuanCarlosOropeza Its an idiomatic phrase that means "no matter what", or "even if it is difficult, I will still (whatever)".
    – BradC
    Feb 20, 2018 at 20:02
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    Did you have to start the examples with ex? I thought those were the ex's accomplishments first and was wondering what you're talking about ;)
    – DonQuiKong
    Feb 20, 2018 at 20:54
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    @DonQuiKong THANK YOU! I just realized that the "ex" was short for "Example" and not "Ex-girlfriend". Feb 20, 2018 at 20:57
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    @adamdavis - there is somewhat of an under-current on SE sites of down-voting answers which don't specifically answer the OP's stated question. Also, sometimes the OP may have stated "I've considered not doing X, but I've decided that I want to, so please tell me how to proceed". And in that case answering "Don't do X" will typically not go over well. I've still written such answers every once in a while, when I've felt that the other side of the issue should be discussed, but understanding that I'll get some push-back from the community. Otherwise, answers like this are fine.
    – AndreiROM
    Feb 21, 2018 at 17:09

There are two separate issues here: how to deal with your insecurities, and how to discuss former partners with current partners. I strongly believe in talking about past partners with current partners, if we feel they are part of our past and they shape the way we are, like we would talk about how we get along with our family or how, say, playing guitar, was an important part of our life and helped us be how we are now. I also strongly believe in sharing insecurities with our partners, because this is a way of being honest and showing our true selves.

This is entirely different from talking about former partners implying any sort of "I'm not over yet" or "I still have feelings" or comparing current and past partners, and I strongly suspect this is what made the three people you dated annoyed. Please be sincere to yourself and think if the perpetual comparison with your ex partner is because of academic achievement, or because you still hold unresolved feelings and issues. If it is a matter of unresolved feelings, you should be sincere to your current partner, and probably break up the relationship or put it in standby while you solve your feelings. If it is a matter of achievement, there is no need to compare yourself to anyone; just make clear (to yourself and to anyone who asks) what your objectives and priorities are, and work as hard as you can towards them. The better you feel about your own hard work, the less you will feel the need to compare yourself to anyone.


I'd like to add to the answer by AndreiROM:

Talk to a friend about this. You can't talk about this with just any friend, you're looking for someone with empathic skills, but also with enough directness to disagree with you when needed. I had a time where I absolutely had to vent some of my thoughts because I was driving myself crazy and just saying them out loud made me realise a lot. I told my friend exactly that that was why I wanted to talk to him and I made sure he knew I apreciated his presence. This person should empathise with you and ask critical questions, the devils advocate if you will.
You should not talk about you all the time though. Don't forget to listen to the friends issues/stories, dont make this a one way relation.

A large part of the problem is probally at your part, you need to find them and fix them. You can do this with self reflection and discussion. This discussion can also be with a professional.
There is a stigma that guys who need to seek help are weak, if that is holding you back, trust me: It'll improve your life.


As a general rule, never discuss previous partners with a current partner.

Most people don't want to know. We all acknowledge that our partners had previous partners, that we are not the first love in their life and they were already not virgins when we met them. (exceptions excepted)

But we don't want to know details. Love is a big illusion and part of it is that we imagine ourselves with the partner and only with the partner. One of the reasons infidelity has such a massive effect on (most) relations is that it shatters that illusion.

Discussing previous partners has a high potential to achieve the same effect. In our minds, we know that this was in the past. Our imagination and our hearts don't have internal timelines.

The Buddhists advise is to focus on the present. The past is past and the future is yet to come. The only thing that is real is the present. Especially when it comes to relationships, that is sound advise.

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    If such a very common thing as sexual infidelities, which usually don't take anything away from the long term partner, are so devastating for this illusion, that often the relationships, which rely on this illusion to be intact, shatter with it, then why not make sure that relationships don't rely on the illusion being intact in the first place? It seems, that this might make more robust and alltogether better relationships... Feb 21, 2018 at 17:23
  • Agree with you on that. In my answer I wanted to focus on how things are, not how they could be different.
    – Tom
    Feb 21, 2018 at 17:47