I usually try to avoid weighing in on topics like this (meaning potentially triggering for someone who is torn about whether to lose weight or not) but giving my usual advice: It is better to lose the weight if you are considered unhealthily overweight. Not talking 20 or so vanity pounds but where your weight either is, or may affect your health (like PCOS, diabetes, heart problems, etc.) regardless of the aesthetic risks. Also most guys tend to pursue women based on our bodies over our faces, I have a sexist theory that women notice a "pretty face" more than men do, men are more about the shoulders and below lol.
As far as "vanity" pounds (the "I just want to look good naked, in a bathing suit, be my weight back in college, etc.) everyone is different but I've noticed a lot of people who only need to lose about 15-20 lbs. and do it when they are over 40, will sometimes look older than they did before. Everyone is different of course, and as
berryblondeboys mentioned it can actually make you look younger to lose the weight. I am in my early 30's (will be 32 in October/2014) and up until 2011 I was getting mistaken for being high school/college age *Whoa* lol, and while I miss it a little bit, age has it's rewards.
I am prepared that I may look more of my age once I hit my goal weight, and I am a big fan of Philosophy Hope in a Jar face cream, at home peels, etc. so I will do my best to weather the storm. Also I am not opposed to getting freshened up w/a chemical peel at a doctor's office once I reach my goal weight lol
, we'll see.