Search Results: what to wear on a date outfit

So I met this guy through a mutual friend and he happens to live out of state. He asked me to come visit him so I booked a flight, which was super expensive, to come see him. I thought since I paid for the flight to come see him and the expensive to look nice: hair done, nails done, new outfit that he would at least pay for the date. He took my to one of his favorite spots and made me pay for everything, (not only my food but his). I'm like damn I came back broke asf. I finally recovering because I just got paid today. Now he's asking me to do the same thing and I just spent all that money two weeks ago. He demands that I come see him this week but doesn't want to go half on the plane ticket. Wants me to wear make up, so I got to get someone to do it for me that $60 just for make up. He wants me buy three new outfits, nails done, redo my hair and I just got it done two weeks ago. I'm like hold up. He wants me to meet his friends so I know we about to go places to eat and stuff and I'm going to have to pay for that too. I really like him but I'm about to ditch him because he's expensive asf.

My boyfriend bought me this outfit for Christmas because I told him I'm always too cold for outdoors stuff and I never ended up wearing it. He said he would love it if I wore it at least once this season, and I never did.

We are going on a skating date this weekend (then walking around shopping, eating), but the problem is it's warmed up considerably and it's not justified. What would you do? Explain below!