Dennie Hughes, relationship expert and columnist for USA Weekend, helps three of Rachael's guests with some unique dating quandaries.

Mandy: "About a year ago I had some 'work' done and I was wondering, when's the best time to bring it up to someone you're dating? Do you let them figure it out, or do you tell them, or do you wait for them to ask you about it?"

Rachael: "Here's some general advice - if the guy has eyes, he can probably already tell!"

Dennie: "Any guy who asks if they're real is not a real man. You did it to make yourself feel comfortable about yourself and if you feel good about yourself don't let any guy make you feel uncomfortable. If that happens, don't go out with him again. Hey, there's 90 million single people in the this country! Don't feel that you have to explain yourself."

Nicole: "I've been doing some online dating. I really started hitting it off with his guy. His online profile looked great, and we had some good banter back and forth. We decided to meet for coffee, and it was a big disappointment. He had no hair - I asked when the photo in his online profile was taken and he said nine years ago! Is it appropriate to ask how recent the photo is on someone's profile without seeming shallow?"

Dennie: "In this day and age of computer dating, there should be no such thing as 'blind dating.' Feel free to say, 'Let's exchange some recent photos.' You should know exactly what you're getting. Make it sound like you're doing him a favor. And if he refuses to reciprocate, you have to know that this guy has something to hide."
"If you've already gone on a few dates with this guy, do not break up with him over instant message or text message -- it's a little bit rude. Wait until he calls you again and say, 'Listen, it felt like we had a friendship connection, but it wasn't a love connection for me. I don't want to date but it was nice meeting you.' Be honest and polite."

Lynne: "I met this really great guy. Through friends, I found out that he collects alimony from his ex-wife. Should I be concerned with this if I choose to pursue the relationship?"

Dennie: "It's kind of a red flag, but you don't know why; you don't know what the situation is. If he's a great guy and you really like him, go out with him. But if he does hit you up with, 'I'm collecting alimony from my wife and I can't pay for dates,' I would say goodbye."

Rachael: "Is there a time limit, or number of dates, when this should be addressed?"

Dennie: "I call it the 'Best Behavior Zone' - the three or four months when you start dating someone. After that, you start to be a little more honest about yourself - you might show up on a date without your legs shaved, whatever. You feel very comfortable in that time, and if you decide to get into a relationship at that point, that's something you will have to talk about. Finances are the number one reason couples break up."