OK, we'll start with the 'tache. I know it's movember, but this really won't do. Wash it off. Lose the specs, or at least get some more trendy ones. Smoking's kind of 'out' with the really fit birds these days, and it certainly won't enamour you with an aerobics instructor (see second illustration), which you will need for getting rid of that bulbous blob of fat around your waist. You might think of wearing a simple, well cut, dark suit; ties aren't necessary outside of work, but always wear simple, conservative, polished black shoes with a suit. Try a different haircut and lose the dye.
Other than that, I'll leave you in the safe hands of Ms Alreadypacked, Ms Norrahe, Ms CM, Ms Poppins and Ms Cojak for advice on actually chatting up a lady. Hint; don't talk about Java coding.