Dear Jackson,

Me and my boyfriend have been going out for three months now, and on the surface, everything is hunky-dory. He’s hot, makes me laugh and we have a similar (perhaps skewed) view of the world. I can feel myself seriously falling for him, but one thing is stopping me from reaching anything gravity-defying yet . . . He’s never told me he finds me pretty. Or anything attractive about my body. It bothers me that he never says it: not when I’m dolled up, put on a new dress, not in bed. Never. I tell him he looks good, but don’t get anything back – now I’m afraid to know the truth. If beauty is in the eye of the beholder, then what does my lover behold?

Beauty is in the eye of the beholder, but what do you behold when you look in the mirror? Do you strike a pose confidently? Or do little imperfections jump out at you? Why do you need confirmation from your man? What do you need him to give you that you can’t give yourself?

For a man, paying compliments to a lover can be frustratingly tricky – I know. If you tell your girl that she’s pretty too often, it can become utterly meaningless through repetition. There was this woman who I lived with years ago. Every morning before work, she would model her day’s outfit and ask, “Do I look good in this?” Me being young and daft, it took me a while to realize that I could never say anything close to no.

I started giving her an enthusiastic “yes” each day, but she began to say, “Oh, you always say that – I want an honest answer.” OK. “Well, your frilly socks and heart-print panties are less ‘risque’, more ‘jailbait’.” Of course, that would make her upset.

Over time, I learned: she wanted an honest answer to the “do I look good?” question, so long as it was a varying degree of “yes”. And if the answer was really and truly “no”, it better damn well be sugar-coated, like, “Why not wear your hot green skirt instead?”

But this boyfriend of yours is clearly on the clueless side of life. My experiences have taught me to be genuine in my praise, and subtle and subdued, when, for example, the outfit really does look awful. Your man, it seems, hasn’t learned a thing.

If you really want to make this work, help him out.

If you’re craving compliments, you should probably ask your boyfriend point-blank what he thinks of your looks. I know you want a genuine and spontaneous “You’re looking fine,” but with this man, I doubt you’re going to get it right now. Give him a hint. Remind him that women like to be told that they look good from time to time. Tell him to be sincere. Don’t be afraid of his answer – if things are going as well as you say they are, he probably (among other things) likes the way you look.

Perhaps he shows you his attraction in other ways. Does he smile proudly when you’re on his arm? Does he boast about you to his friends? Does his desire for you manifest itself in wild tangled nights in bed? Lacking eloquence, many men opt for the “show, don’t tell” approach to complimenting their lovers. Gentlemen, can you hear me? This doesn’t work.

But help yourself too and think, do you really need to be buoyed by the occasional complimentary utterance? Where’s your self-esteem? Behold yourself as beautiful too, and this little problem you’re experiencing with your man might seem a lot less significant.​