03/21/2013 05:35 pm ET Updated May 21, 2013

Why Dating Should Be Easy... Like Sunday Morning

Last week I went on a date with this guy I met at Soul Cycle. We met up at a cool wine bar in Hell's Kitchen. It was super cozy. He had great manners, pulling out the bar stool for me as well as ordering for me which I thought was cute. The bartender knew him well and loaded us up on lots of wine. We chatted for hours and got a little drunk together. When we walked out he said he had a great time, gave me a hug and we went our separate ways. I never heard from him again. This happens often with dating and I'm frustrated. Help! Michelle P, New York City

Don't sweat this. He did everything wrong and you have a few things to learn as well. First, I tend to bet the reason he knew the bartender so well is that you aren't the first date he's brought to said bar. Of course you chatted for hours, you were both drunk, which is something you should never get on a date. You're bound to say something you shouldn't have (which you may have done) and drunk people are really not attractive. In this case, it doesn't matter because he sounds like a loser with no manners. You should have given your wine preference and, instead of applauding his pulling out the bar stool for you, he should have put you in a cab to ensure your safety. He should have not given you one of those awkward I-don't-know-how-to-say-goodbye hugs and walked away. As for people in the future not calling you back, you have no idea what else is going on in their lives. Take this lesson I learned -- the world doesn't revolve around you -- although I know it would be nice. When you meet the right guy, it will be seamless. Next time you go to Soul Cycle, spin, honey, spin. You'll feel a lot better about all this.

I'm a really successful woman working in public relations in NYC and am finally dating someone. Work has always come before dating so I'm feeling good about having met someone I really care about. However, there is one problem. I think the guy is a little shady. He says he's a stock broker. It's been three months and he never talks about the stock market. I have never seen his condo or met his friends and I only see him once or twice a week and the date is over by ten o'clock. Is there something to worry about or is he just taking things slow? Name Withheld, NYC

At first, I thought this email was a joke. But you responded back and because you seemed genuine, I do have advice. Never ask me to be your partner on The Amazing Race because clearly, you don't know how to read a clue. Seriously, for all you know he could work in a pizza parlor and live with mom in Queens or maybe he's got a girlfriend at his so-called condo. Dump him (although I'm not sure he's dating you) and stop complicating your life with guys like this. Get a guy whose apartment you sleep over at and whose friends you enjoy eating Sunday brunch with. One more thing, stop with the "I'm a really successful PR girl" shtick. It's really annoying.

My sister has become an obsessed dater and it's making me crazy. A month after breaking up with her boyfriend she's on Jdate, Match.Com and OK Cupid. We used to go out at least two, three times a week. Now I see her about once every two weeks. When we're together she has her face in her phone, yet she doesn't share any of her stories. Clearly, she's going through something and I don't think turning 39 has helped the situation. I am not sure what to do. Clara, Los Angles.

Your sister is living in a state of desperation. I have a girlfriend like this. She was going out almost nightly looking for "Mr. Right." When she finally broke down and asked me why nothing is working and what's wrong with her, my answer was a bit in her face but true -- desperation is not attractive and men can sniff it out like a hound dog. That's what's happening with your sister. I also advised my friend to go out with guys she knows she likes, not the ones she could learn to like. Don't nag and become that annoying sister and whatever you do, don't judge and suggest she see a shrink. Instead, give her an early holiday present like a relationship expert, which is very non-threatening. She needs this because she's stuck in her own head -- another reason she isn't sharing. When she does, always be there for her.

I love the Style section of the Huffington Post and I love advice. So here is my question: I am 25-year-old gay guy and I'm looking for my soul mate. I am hopeless romantic and I have been dating a lot. I feel so blessed to meet a lot of guys that are really awesome, but nothing is clicking for me. I give a lot of myself and just ask for that back! I'm getting sick of it! Luke L, New York City

Glad you like the Style section. However, I'm not sure about the exclamation points and the "I'm so blessed thing." Lots of people out there would be only too glad to meet a lot of guys. Anyway, you're only 25 -- date lots of people and experience lots of things. Enjoy getting to know yourself and finding out what does and doesn't work for you without asking back the same you put in. Experience will enable you to know a good thing when you find it -- stop trying so hard and enjoy all those men.

Want some simple advice? Contact me at mcnewyorkcity@gmail or leave your comments below.