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A very dear friend of mine has low self esteem, particularly relating to social desirability and men, and becomes very sad when I've expressed my deep appreciation for her. Compliments just make her feel that it couldn't possibly be true and she's even cried when I've told her that I love her and appreciate all her support during difficult times. I now believe that this is causing some distance between us that I'd like to remedy.

We dated last year, so I realize that complicates things as there are likely unresolved feelings. My goal isn't to resume this aspect of our relationship though, as I suspect it's still not viable. I merely want to build our friendship because I value her immensely as a person.

I recognize I'm not her therapist and I'm not looking to fix her low self esteem. I'm also not being an armchair psychiatrist; she's told me how she feels and why. If culture is relevant we're both American from progressive/urban regions but her parents are Indian Punjabi immigrants and Sikh culture certainly influenced her.

How can I express positive sentiments towards her without triggering her low self esteem?

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    You seem to be asking multiple questions at once, please limit your question to only one case/question at a time. Also, please get rid of the disclaimer. Answers that say 'don't' are allowed here anyways... – Tinkeringbell Feb 7 '18 at 15:59
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    @WilliamGrobman Take a look at this answer, it also explains that saying 'you don't, here's why' is perfectly valid in cases: interpersonal.meta.stackexchange.com/a/1497/1599... – Tinkeringbell Feb 7 '18 at 16:14
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    @WilliamGrobman if you want to leave it as is, feel free... people might close it as too broad though. Thanking someone, complimenting someone, expressing fondness/affection are all very different things in my opinion... – Tinkeringbell Feb 7 '18 at 16:15
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    @Tinkeringbell is the question really about thanking, complimenting, expressing fondness, or is it about the reaction from someone with self-esteem issues? – apaul Feb 7 '18 at 16:28
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    I have to say I agree with Tinkeringbell on the "too broad" part. I would love to answer the point about "how to compliment someone with low self esteem", but I can't speak to the part about expressing affection towards someone you used to date. – Em C Feb 7 '18 at 16:28
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How can I can be a good friend who doesn't take her kindness for granted without triggering her low self esteem?

The short answer here is that you really can't. I know that's rough, but people feel how they feel, and you can't really control their reactions.

What you can do is be genuine. People with self-esteem or confidence issues tend to assume the worst, so if you try to mitigate their reactions and feelings it'll likely be read as a manipulation. Their natural inclination is that "you're just saying that to make them feel better" coding your words makes it easier for them to conclude that you're not really saying what you mean.

How can I express affection/fondness for her without upsetting her?

Again, just be genuine, and don't try to control her response.

Be aware that since you two had a previous romantic relationship that didn't work out, she'll likely be particularly sensitive to affection coming from you. I'm not saying that you shouldn't be affectionate, just be aware of the lines between friendship and romantic entanglement. Be careful about what signals you're sending.

How can I compliment her intelligence/character/ability without making her feel worthless?

Again, be genuine, but here consistency can help. Offer compliments whether she's feeling up or down, whether she responds well or not. You're expressing an opinion, which doesn't hinge on how she feels about it.


I know you want to help your friend, and I'm glad that you already acknowledge that you can't be her therapist. I've had a good many friends that go through, or went through, phases of low-selfesteem. Some people get down for a little while and bounce back when their circumstances change, but some sorta get stuck there and need help to pull out of it.

If your friend has been stuck for... more than a while, she may need professional help. There's no shame in that, loads of people need a hand and seek it out, hell I'm going to see my shrink later today.

Be gentle if you decide to mention seeking professional help. Probably better to bring it up if/when they're already talking about their problems.

Lots of people have those issues and lots of people find some relief talking to a therapist/counselor/psychologist/psychiatrist. There's no shame in asking for help. I mean, you're asking me for help right now. It's just asking someone who's got more experience and training.

  • I'm looking less to help her with this problem as much as not exacerbate it with my natural communication style, which is being expressive about your feelings for those you care for and complimenting people's virtues and accomplishments. I don't want to control her response but be sensitive to her feelings. I'm expressing these things in a way that isn't productive and I'm not sure how to adapt. – William Grobman Feb 7 '18 at 17:30
  • To clarify, my reason for doing so is that I think she has a handle on it and has sought appropriate help when needed before. – William Grobman Feb 7 '18 at 17:32
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    @WilliamGrobman I'm suggesting that adapting may end up being somewhat counterproductive. Just be genuine, and if she seems to be struggling significantly suggest seeking professional help. – apaul Feb 7 '18 at 17:38
  • I understand your position better now. I see what you mean by saying it could come across as manipulative if I'm tailoring my comments to avoid upsetting her. – William Grobman Feb 7 '18 at 17:42
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Some people with low self-esteem just don't accept praise and compliments from friends and logically square that circle by telling themselves "they're my friends; they have to say that." It's a hard loop to break out of.

I think that the best option here is to be sincere with this friend. Say what's on your mind, but above all be truthful. There's another post on this site that I find related: how to recognize false praise? I'd suggest looking at that and avoiding the things that make your sincere compliments seem false.

In response to your specific questions:

  • This is tough. But when she is kind, recognize it if appropriate. Respond with kindness as well. Don't overcompensate; she'll see through that or, in a worst case scenario, will see that overcompensation as normal and be disappointed when others don't do that as well.
  • Do things that friends do. It sounds like there is a terminated romantic relationship here, so the challenge is to be friends without rekindling that romance. So I'd suggest doing things in groups and being very careful to not send the wrong message.
  • Unless she does something extraordinary or excellent, this can be a real mine field. Share in her joys and successes but don't gush. Help her realize what her ability and hard work enabled her to do. Again, don't overcompensate. You're her friend and not her therapist.
  • I think you might be right for general approach. I think that showing my appreciation in the first case through mild verbal thanks but more through returned kindness is a better idea. You might be right that the second category is tugging at the heartstrings and I'll be more mindful there. I think I'll need to work on the third one though and will look at the linked question for tips. – William Grobman Feb 7 '18 at 15:43
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This is big.

I'm in the exact same condition of low self-esteeem as your dear friend, so I apologize if I might sound biased, I apologize if this all might sound harsh and I apologize even more if you think this answer will be utterly unhelpful, nevertheless I feel compelled to answer as sincerely as the top of my heart can.

I'll now analyze your post (both premises and questions) by breaking it down in points and answering point by point.

Compliments just make her feel that it couldn't possibly be true

Because, actually, they might be not true. "You have two beautiful eyes" is subjective, what is beautiful to you may not be to your friend. "You're soooo good at computers" is also subjective: you might have a lower understanding of computer science than your friend's one so you possibly can't assess whether your friend is actually good at it or maybe just an amateur.

Please, try to accept that you might actually be wrong, and therefore your compliment can be wrong likewise. You're in your own shoes, not your friend's ones.

Therefore what you see as true your friend could perceive as false. By the way you generically used the word "compliments" I assume you already tried this step a number of times and it didn't work, so you may want to try to give this one up. You two are likely on very different perspectives/points of views/opinions that cannot be reconciled. And by keeping on grasping on your own views which your friends disagrees from will only put additional strain on the relationship.

We dated last year

Whoa!

This is devastatingly bigger than anything else in this post. The end of your dating period is extremely likely to just represent one more reason for which the self esteem is low and the perceived desirability from men is low. You are one who went on an unsuccesful dating period with her and at the same time you want to be the one giving her confidence about desirability from men? Please, imagine this logical mental process of hers: "Hey, how can YOU tell me I am desirable by men if YOU, a man yourself, desire me no longer?" Let men other than you talk to her about this subject, because you represent that part of men that considers her undesirable, you'd be lacking coherence severely here.

I merely want to build our friendship because I value her immensely as a person.

As per my own experience and that of some friends of mine, a friendship after a dating period is not always possible. She might not want what you want, regardless how much you value her.

Therefore, try to not take for granted that you can actually be a good friend. Which leads us, eventually, to your questions:

How can I can be a good friend who doesn't take her kindness for granted without triggering her low self esteem?

How can I express affection/fondness for her without upsetting her?

How can I compliment her intelligence/character/ability without making her feel worthless?

Please notice that she may not want it, and she may communicate it not explicitly. It could also be inconscious to her that she doesn't want to you to be her friend.

So, before asking yourself "How can I...", try asking yourself "Can I...", because you may not be the one who can help her, as bitter as it can sound.

My suggestion (talking as the one who relates to her feelings): give her space and time. Regardless whether you are acting on good heart and true good feelings toward her, help from you is not working as she keeps on rejecting it, so all you can do is taking a break and giving her the same break. Take a distance and keep it for a while. She will be in the position of not being able to rely on your "help", which will lead to two possible outcomes:

  • she will be fine with that distance and won't come back: it will be the sign that, regardless of your good heart, you where more of a weight (on her already strained self esteem) than a helping hand. If you do love her and value her, as bad as you can feel about it, let her be. Dalai Lama says "[...] if you can't help them, at least don't hurt them."
  • she will come back: that will be the sign that, regardless of her on-the-spot reactions, she enjoys how you compliment her, hence you can come back to assist her as naturally as you feel, because she did decide to deliberately come back to that assistance.

A final consideration: personally, I prefer facts than words. Facts are stubborn; facts are strong and, conversely, words/opinions are weak. If she's any like-minded to me, only things that will heal her self-esteem will be facts, e.g. a suitable man actually approaching her and actually successfully building a love story with her, thus actually proving her she is worth.

Wishing all the best for both her and you. :)

  • After we split up she took space and time before reaching out again. We've been rebuilding the friendship since then. My goal is not so much to help repair her self esteem or validate her through my approval. It's simply to be sensitive to her feelings and avoid paining her so that our friendship can grow. It seems my natural communication style is somewhat burdensome and I want adaptation advice. – William Grobman Feb 7 '18 at 17:37
  • I do recognize that even though she reached out, she may not be able to be friends with me, even if she doesn't realize yet. That's on her to decide though. All I can do is be as sensitive to her feelings as I can and treat her well. – William Grobman Feb 7 '18 at 17:40
  • @WilliamGrobman "simply to be sensitive to her feelings" -> you have already proven this very well, by being there for her. The whole point here, therefore, is not what you say and how you say it: the problem is that your very "friendship" might not be the solution, also possibly due to those unresolved feelings. You let her recover from the dating, but then you attempted a friendship: because it has not worked either, now it's time to see whether she actually wants a friendship back or if she lives by the "either dating or nothing" rule. – Markino Feb 8 '18 at 8:08

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