I am coming out of a relationship situation where I paid for EVERYTHING and then some. It was very draining because I was a college student and he had a salaried job.

ANYWAY, here is the background on the new dating situation:

This new guy I am dating is 36, very attractive, out-going, fun, athletic, nice, recently divorced, college educated, and works as a Project Manager for a construction company. I am 22 and a college student who lives well in a very posh area but only because of the support/dependence of my parents. I have no job and because of my previous relationship my parents do not give me as much FREE money as I once had.

THE NEW GUY has paid for the first 3 days. I am going on a forth date this Thursday and I am beginning to feel out of my element. I love the fact that he is paying for me, I feel so special. On the 2nd date we were having fun and made a playful bet. ( I said I wanted a cupcake if I won and he wanted a kiss if he did). We decided to raise the stakes and he if he won he wanted a full body massage and he asked me "What is something that I really wanted?" I said. "I want a new handbag." (it was a Louis Vuitton and he later stated he had no problem buying it for me if I win). Not sure if that is strange or not, but whatever. He has made many NUMEROUS flattering comments about my appearance and how I carry myself. He finds me to be sexy, intelligent, sophisticated, elegant and beautiful.

The reason I am saying all of this is because I am trying to paint a picture so I can get the best answer. I am having a good time with this guy, but I am worried about the paying arrangement. He doesn't cook and he stated that he eats out almost all of his meals. I am so used to paying but he seems to enjoy my company. He initiates all out our outings and he knows I am an unemployed college student. I don't want to come off to him as a user or opportunist, but am I really excited about this dating situation. I am worried that if I offer I will end up like my last one. He drives 30 minutes to see me for our dates and the 4th date will be the 3rd time this week. Should a guy always pay?

The man shouldn't always be the one to pay, but considering he is the one with a full time sustaiable job, compared to you who- a struggling college student I guess it's not really a major problem if he is the one to mostly pay at the moment. I am sure that he doesn't mind and understands that you can't afford to fork out the money. If he really had a problem with it (which it doesn't seem like he does at all if he keeps asking you out!) then I'm sure he would let you know!

Maybe instead of trying to get money to pay to take him out somewhere you could pack a pinic or something and go to a nice park to surprise him? That way it's not as expensive and can still be a really nice outing! It's the little gestures that really matter, not necessarily who pays for what!

WOW you are just full of good ideas tonight! Thanks for your advice. That would be a really cute idea and the weather in Atlanta would be perfect for it! So should I offer anything on the fourth date ( like paying my half, tip, or the entire thing?) Or should I just let things continue the way they are?

I'd say at this stage just let it continue the way it is going and tell him that for your next date you are going to be the one to surprise him and take him out! (That's when the picnic comes into it!) :)

Sounds good to me! Thanks!

No worries! Good luck with it! I hope it all goes well!

Its one thing to remember our mistakes of the past, and another to not let them haunt us in the present.

I think you should go with the flow, and let him lead for a while, and enjoy it.

Its okay to let him pursue which no man minds, as long as he knows you appreciate the attention.

Down the road you can step up, and treat him, if things continue, but for now just see if he is worth it, after this continues a bit. He knows your situation, and if he is sincere will not expect anything but a great fun time from you.

That picnic sounds like a great idea, but I would hold off on breaking the budget for now.

Thank you. I think that is a good idea. I just did not want to appear like an opportunist, but I can follow his lead for sure.