Interesting dilemma,
Two weeks is a long time.  Most people don't get that much time along with their spouses or s/o's.  I assume you have done overnights or shorter trips with him.  In your second paragraph, you called him your suitor and not your client, how do you really feel about him?

Do you eat the same things he does? Are you staying in a single hotel room or will you have space to be apart even when you are together?  Can you sleep with him or does he snore?  How much "me" time do you really need.  Can you bail out mid-trip if you need to?  What if he wants you to bail?

All the little things about a person we tend to overlook get magnified over that long a time particularly if there isn't any one else to buffer the only person in Milan you are going to know.

I personally would go for it but it also sounds like if you survive this, the two of you will be ready to move in together.

Good luck

The central old city of Milan is interesting but that will take a day or two to see. Will you be able to rent a car and explore the surrounding area? That would be a big consideration. The Lake District is beautiful but two weeks in Milan even with someone you want to be with may be a bit much.

Milan is beautiful, but two weeks is an awfully long time.  Unless you two are really, really compatable with each other, it will probably be too long a time.

Anyway, I hope whatever decision you make, works well for you.

Cheers!

Re:HELP!!

I think you should go for it!

You won't get bored by Italy.  While Milan is not the most beautiful of Italian cities it is set in a most beautiful countryside. Rent a car and look around.. Italian trains are quite good, although not superfast... they will get you to other cities quickly.

In Milan you have wonderful art and architecture.  If you are not into churches and Leonardo's Last Supper you will be looking for other things in a few days.

The Italian Riviera is in striking distance.  You can drive to Genoa (1.5 hours) and then on to Pisa (3.5 hours) Or turn the other way at Genoa and go to San Remo and Monaco (3 hours).

Well I feel bad now.  I hope your suitor is not a TER reader.
Be hard to have all this extra help he never asked for.

You should go.  You will have plenty of "me" time because he is going to be working.  Most of who work would kill for that much time to ourselves.  You can explore, read, write, stay late in bed.  He presumably is going to have to perform at work so he can't possible expect to be out carousing till all hours of the night.  So sounds like a pretty easy time.

Anyway what do you have to lose other than time and you may really learn something about yourself

Hey Corii -

My ATF and I went to Milan and Naples for two weeks back in 2001.  We had an absolute blast!!  Milan's a great city, plenty to do and see, world-class shopping and fashion, culture, arts, restaurants, music and clubs, etc.  You will definitely not get bored.  Got a great price break from ATF (she wanted to make it happen) and we just cruised through the two weeks - it went by like a flash.  My advice - if you get along with the guy and feel comfortable, then give him your best 'preferred client rate', deliver the real 'girl friend experience' for more than an hour at a time, get on the plane, and go enjoy life.

good luck

RVW

Thanks for all the advice

I just want to give a BIG "Thank you" for all who gave me feedback.  I am going to go for it.  It is in the month of August so I have time to prepare.

Yes, he is definitely a regular client, and has been since I started in the biz.  He is a real sweetie pie, and I don't think I would have a problem at all - just never spent more than a few days with him though!  He is saying two weeks, but possibly shorter.  I will make the best of my time there, both with him and while alone!

Thanks again,
Corii