For our special TV iLiving in a style-conscious city like Toronto gives one ample opportunity to hook up with your next significant other (or temporary fall fling). And who better than Sheldon Calender, co-host of the hit “pickup” reality series Keys to the VIP, to give you advice on making that all-important connection. Calender answers Sway readers’ most pressing relationship questions.

(The player-istic opinions expressed here are not those of Sway magazine. Ladies, read at your own risk.)

Should I pay for the date or should he? Sharnette, 27, Rexdale

“My rule is three dates and a punk fake. On the first dates I’ll pay. On the third date I’m still paying, but she has to at least reach for her wallet and look like she is going to offer to pay. If she doesn’t make that attempt, it tells me that she sees me as a source of income. I want her to see me as her equal. I want to know that she is also investing something in the relationship. It’s shouldn’t just go one way.”

How should I act on a first date? Michelle, 19, Brampton

“It’s quite painful to get shot down. Guys are just as insecure as women. Stroke his ego. Make him feel appreciated. Guys don’t always know how a date went. Tell him you had a great time. Since you didn’t invite him back to your place, he’s not sure what to think.”

How long will it take before I know if he’s the one? Nicole, 29, Scarborough

“Look ladies, just enjoy the journey. The problem is that women want to land the husband every time they go out. If you date two or three times and the guy is paying most of the time, what’s the problem? Just enjoy it. And if he’s not for you, move on to the next one.”

What should I look for in a guy? Stacey, 24, Toronto

“Some women have a long list of things they want in a guy. But what they really want is someone who is going to love them for who they are. Say less about what you want. Just wait and see if the guy has the characteristics you are looking for. Let him be himself and see if that works for you.”

I’m a career woman. How do I get the man of my dreams? Melissa, 33, Toronto

“I hear women say, ÔGuys are intimidated by me because I’m a professional and I know what I want.’ But why do you have to tell him you’re a professional and you don’t have time for this or that? It’s almost like saying if you’re not going to be my husband on the first date, don’t bother me. That’s intimidating for a guy.”

OK, I’ve looked everywhere! Where can I meet a good man? Keisha, 31, Pickering

“Quality guys are everywhere. If you want to meet guys, walk into work and say “hi” to every guy on the elevator, every time you go up the elevator. It’s not that you want to date all of them, but you are letting them know you are a very personable person.”

Watch the guys try to pick up the ladies: