1. Compliments will likely not solve things. Give them out, but be absolutely honest. Don’t look at them fresh from doing yard work and tell them they’re gorgeous. What usually comes with a low self-image is an increased intelligence and an increased skepticism of politeness or flattery, and you will be called on your bullshit. If you do find them at their most beautiful covered in dirt and dead aphids, tell them in the clearest terms possible. Platitudes and synonyms for “pretty” will not do. Have details and evidence. Show that you’re being more than nice to set them in a good mood.
2. Bring out your own issues. Criticizing yourself on the same small details which drag down their mentality can create a kinship that can be helpful to both partners. Listen carefully when they are stressed about their own behavior, their appearance, the security of their financial situation. More often than not an open ear is the best attitude to have, but relating on similar troubles shows both of you that you are not alone and why you are not alone.
3. Encourage relaxation. Realize their self-criticism comes from a place of concern for being a good person, that their motives are not for pity but for survival, and this results in a constant need to fulfill every responsibility before they think of themselves. Remind them that not everything must be done this instant, that it is often okay to be selfish and sit on the futon eating Fritos dipped in hummus watching Weeds. The laundry is not going anywhere in an hour or two. There will always be things to do, responsibilities to fill, a few cups in the sink.
4. Note their anger at others when they feel judged. Realize they are criticizing their co-workers or family members for saying the same things they say to themselves. They will simultaneously call themselves stupid and get angry at clients for treating them like they’re stupid. Lightheartedly note this hypocrisy to them, that somewhere beneath the stress and sweat is the realization that they are a good person, they are doing their absolute best. Realize they are self-critical because they feel the need to be before others are, so no one can hurt them worse than they can hurt themselves. Remind them it is an immature and dastardly heart that spends more time looking out than looking in.
5. Ask what they want. It is easy to become awash in their need to please and prove they are not selfish that you may forget they have desires as well. Where do they want to get lunch, what movie would they like to see, do they really care to go to your class reunion? They may be afraid to speak up for fear of upsetting you or building future ammunition for a hypothetical argument. Talk past that. Smile and push them to divulge what they want. Remind them this is not selfish of them, they will never be attacked for this, this is what affection looks like.
6. Never take their mother’s side. Never.
7. Confirm how incredible they are. Hopefully, you’re dating them because you think they are amazing and worthwhile. Let them know this. Give a never-ending list of reasons for your affection: their quest to be the best person they can, the intense work they put in to being themselves, the work they do every day for which they eschew dreams and pride. Low self-esteem is an existential issue. Confirm their precious existence, the meaning of their most difficult actions. If you even feel the word “needy” entering your mind, remind yourself of why you are with them by reminding them.
8. Never ever ever take advantage of their self-hatred. While reminding them of how unbelievably momentous meeting them was, remind yourself that you can never break the trust they have built by sharing that with you. Someone who hates themselves typically feels this way after having any number of people break the trust that comes with letting someone in. Do not join their ranks. They are giving you an immense gift by allowing you to get to the know them, one they rarely allow themselves. As is true in any relationship, physical touch and emotional intimacy bestows great meaning upon you, and any judgement you make could further deepen them into the bowels of agony induced by the type of asshole you must not be. A healthy relationship must share both vulnerability and trust, something they may have offered you but you must absolutely offer them. Do not lock yourself away, do not ignore their feelings, do not be annoyed. Patience is of the utmost importance, and if you feel it a waste of your time, you are probably wasting their time as well.