Advice

It's fall! That means it's time for another quick 'n' dirty style advice column. Oh yeah. If you missed the last one, read the summer quickies here . I'm so awkward at parties! How do I make conversation without looking like a doofus? Approach people who are alone rather than in a group because you'll be less intimidated and you'll get that person's undivided attention. Ask basic, neutral questions: "Who do you know at this party?" "Is that a Mexican car bomb you're drinking?"

I'm wondering when is the best time, and how, to tell a prospective dating person that you are in a polyamorous relationship. Obviously before any physicality, but in a more granular sense, when? Call, text, first date?--Poly Wanna Answer When it comes to potentially delicate subject matters, I've found it's really best to say it with a cake. Or, if cake's not their thing, then a really large cookie, the kind that come in those delightful mall boutiques next to Orange Julius. Nothing says romance like “My penis likes you, just not exclusively!

My boyfriend and I want to incorporate sex toys into our lives but we're both newbies. It seems a little embarrassing to walk into a store, especially because we don't know exactly what we're looking for. Do you have suggestions? - Newb I know how you feel. Like eating at a taqueria where the menu is written in Sharpie, buying sex toys is always kind of a gamble, regardless of how helpful the sex store staff may be (that's not a euphemism). That said, I have total faith that you and your boyfriend will triumph in your new adventures in Silicon Valley (that is a euphemism)

I cheated on my boyfriend a year ago. We broke up for other reasons, but I still feel a lingering sense of guilt about what I did. Should I tell him about it or let it go? We talk and stuff, but I wouldn't say we're friends now exactly.--Too Little Too Late Unless it's to inform him about a strangely belated case of the clap, don't tell him. A confession this late in the game is pointless; it's just going to reopen an old wound that doesn't need to be opened. Doing so would make you feel better, but him feel worse.

I've been out of the sex game for a while, save for a very casual relationship that happens sporadically. However, I met a girl recently and sex is imminent. I'm excited about it but worried because I'm having a hard time letting people touch me, just relaxing and enjoying sensation. My last relationship was largely sexless and took a serious toll on my ego, and now the little sex I have had in recent months is fraught with anxiety and over-thinking, and I don't want that to happen this time.

I have met this girl a couple times and I find her to be very cute. The last time I ran into the girl, I got tongue-tied and didn't want to make myself look dumb. Now I was thinking that I could go and search for her on Facebook and see if I can do introduce myself that way. What do you think? Or should I go about it in another way? - Lost and confused It's not the most direct route, but Facebook is a perfectly acceptable gateway to your crush's heart. I know because I've done it m'self a few times.

I'm 28 and a young man of 21 has been showing interest in me. I have known him for many years because he lives two blocks away and his parents are friends with mine. I also have a 19-year-old brother who looks up to him. I have been getting to know him, but we have yet to go on a date. I'm nervous about it. I am attracted to him and would like to give him a chance, but sometimes I think this could backfire. He is very focused on school and he works full-time, and from what I know is a really good person.

My girlfriend and I were together a little less than a year before we decided to take the plunge and live together. We both felt that it was a good idea because we eventually saw this leading to marriage. However, it has really backfired on both of us. We argue on a weekly and sometimes daily basis. Some of them have been pretty intense, but we have always made up. Although, I believe the reason for this is only because we know that we live together. Before living together, I would say that we had a pretty healthy and active...

Leave your answer in the comments box, and you might find yourself in a future issue of RedEye. Follow @redeyesportsguy for daily details about Five on Five openings. 1. Scoring five power-play goals in one game is like … 2. What's your substitute for watching NBA games? 3. The Bears are to “Monday Night Football” as … 4. Give Carlos Zambrano some advice for pitching in the Winter League. 5. Whom is this quote about: “He's a special dude”?

Do you suck at being in a relationship? Wonder why the so-called love of your life left you? Are you too picky to find Mr. Right? Sounds like you're in need of some " Tough Love . " The VH1 reality show is holding a casting call for women ages 23 to 39 from 10 a.m. to 3 p.m. Dec. 3 at Moe's Cantina in River North. Dating coach and matchmaker Steve Ward talked to RedEye about heading into the show's fifth cycle of dating boot camp and his thoughts on deal breakers, dating faux pas and gift giving.

I've spent the last year-and-half dating dudes from OKCupid, but now I'm in a place where I'm looking for a more serious relationship. I've been looking for alternatives to OKC, as well as meeting dudes IRL (in real life), and I've been thinking that JDate would be a good match for me. I was raised Catholic, and my family still celebrates Christmas and Easter, but I find that I have the best relationships with Jewish guys. What's the etiquette for joining a site like this when I'm not actually Jewish?

I've had a booty call relationship with a guy for a while. I haven't seen him in probably two months, but we used to hang out every couple of weeks. He's been texting me a lot recently to meet up, but I'm not interested in casual sex anymore. (I'm looking for an actual relationship). We don't really have a lot in common outside the bedroom, so it's unlikely we'll be friends. Do I have to “break up” with him? If so, how do I do it without hurting his feelings?--B.C. Blues A few years back I went on a date with a girl.

I am single and actively dating, and I recently received some advice from male friends that I should make myself less available to the men I date and try playing hard to get. My question is, does this really work? And if so, what are some effective strategies? - Mouse Seeks Cat You know, I was all prepared to launch into militant all-caps speech about how honesty is NOT JUST A TEA BRAND, but there is research that suggests playing hard to get does work in some instances. In a study published in the European Journal of...

Is it possible to support same-sex marriage at the same time that I don't support marriage in general? I respect and love my gay friends and certainly wouldn't want to deny them any of their rights, but I've never believed in marriage as an institution, and I find myself at odds. --Confused but Hopeful Dear Confused, For those of you who have missed all the hullabaloo and the red equality signs on Facebook and Twitter, the Supreme Court has been hearing two gay rights cases this week: Prop.

I don't normally use my massive platform as a cultural and political force here at the 16 th highest trafficked blog at RedEye to stick it to individual companies. After all, in the pursuit of a reliable and profitable business, all companies make mistakes. New Coke, Starbury sneakers, the George Clooney Batman movie - bad products surface. Yet after ordering lackluster Chinese food with a friend the other night, I fear I cannot maintain silence on this one. No, it's not the lackluster Chinese food establishment that sparked my white-hot ire,...

Welcome to spring! It'll still be cold for two more months , but that doesn't mean we can't dream about putting our ski masks away and of summer hookups to come. With a new season comes a new quick 'n' dirty column , advice for the short of attention but long of time-wastiness. My really good friend is in a sticky situation. He and his girl have been dating for about four months, and they're perfect for each other, but she's moving to Africa to go into the Peace Corp for two years!

It's NCAA tournament time! And that means brackets. Almost everyone fills one out, but what is the best strategy? And should you even strategize, or just pick the high seeds? Well, RedEye found four people confident in their bracket skills and picked their brains on their bracketology methodology.   Paul M. Banks, 35, Lakeview, @paulmbanks Illinois alumnus Owner of TheSportsBank.net "I've won two pools in the past five years: one had more than 900 participants.

My girlfriend and I were together a little less than a year before we decided to take the plunge and live together. We both felt that it was a good idea because we eventually saw this leading to marriage. However, it has really backfired on both of us. We argue on a weekly and sometimes daily basis. Some of them have been pretty intense, but we have always made up. Although, I believe the reason for this is only because we know that we live together. Before living together, I would say that we had a pretty healthy and active sex...