Boost his ego.
Tell him the reasons that you like him. Tell him what you find interesting about him. Let him know why you feel the two of you make a good couple
Tell him that you find self-loathing incredibly unattractive.
Men with low self-esteem will sometimes tell their dates that they are not worthy of dating beautiful women. They often refer to themselves as ugly and not worthy of having a good relationship.
Change the topic of the conversation if it takes on a negative tone.
If he makes a negative comment, such as "I'm too dull to date you", pay little attention to it. Smile, shrug it off and say "that's the silliest thing I've heard. " Ask him about his hobbies, favorite books or favorite bands.
Give the guy a chance once you have firmly stated how you feel about his self-loathing.
If he continues with his self-loathing comments and negative outlook, it's your choice whether to continue dating him. Dating someone who is always putting himself down can get depressing after awhile.
Smiling will show him that you enjoy spending time with him.
Be prepared for the possibility that dating someone with low self-esteem may require you to constantly boost his ego.
Ask yourself if you are willing to compliment him or prop him up him on a regular basis.
- Never date a man just because you feel sorry for him.
- It's not your job to fix the man you are dating.