Help me, Cupid! I need matchmaking assistance. I matched with 21 local lovelies. Which should I contact?

Don’t say “all of them,” as I don’t want to be “that guy” yet.

Cathy will help me decide on today’s Nice Guy Show at 11am PST. Feel free to dial in and join us (347) 237-4721.


Your Guide to Group Dates

With all the disappointment surrounding most one-on-one internet-arranged blind dates, let’s welcome a new way to meet people: group dates. Think of this as the buffet of the dating world. Instead of being stuck with a meal (mate) the waiter (website) recommends because it’s about to spoil (hasn’t been laid since white belts were cool), you can browse the buffet until you satisfy your appetite.

Typical complaints I hear regarding dates arranged by traditional dating sites include:

  1. He was ten years older than he claimed–maybe twenty.
  2. She was twenty pounds heavier than she claimed–maybe thirty.
  3. He was four inches shorter than he claimed.
  4. She had ass breath.
  5. He wore leather sandals.
  6. She downed four drinks before dinner.
  7. He must have showered in cheap cologne. I smelled him from the parking lot.
  8. She spent most of the date staring at her iPhone.
  9. He was expecting to have sex after dinner.
  10. She had man hands.

This can all be avoided on the group date. When stuck next to a dud, excuse yourself and move down the buffet to the next item, Sugarsnack. Keep in mind there’s a certain decorum required in the group date atmosphere. It’s not quite as awkward as the one-on-one date, but you don’t want to show up unprepared. Let me help.

Date preparation do:

  • Cleanse thyself.
  • Trim your fucking nails. (Sorry, that’s a pinch point … in fact, “pinch point” is a pinch point.)
  • Mute your phone.
  • Iron that top–sleeves too.
  • Whiten dem teefs.

Date preparation do NOT:

  • Eat garlic within 24 hours.
  • Pre-Stalk the attendees.
  • Ride a bike to the date, unless the date involves a bike ride, in which case, why are you going on that date?
  • Be the first to arrive.
  • Wear all white or all black.

During the group date, do:

  • Smile.
  • Ask others about their interests.
  • Laugh at jokes, even when not funny.
  • Pull chairs out for ladies.
  • Be subtle when checking out boobs, butts, hand sizes, etc.

During the group date, do NOT:

  • Avoid alcohol, but don’t get shickered (yes, that’s a word) either.
  • Begin every sentence with “I …”.
  • Attempt to play footsies.
  • Allow rivals to know your target.
  • Talk about Jesus, Romney, your roommates, prison, or that “thing” you had removed.

After the date, do:

  • Tell people it was nice meeting them, without asking if you can mate soon.
  • Keep a positive attitude. Consider it a success, even when no condoms are involved.
  • A little research by Googling those who grabbed your interest. If you find a lovely picture and have an irresistible urge to release yourself, please close the blinds and never confess it.
  • Tip generously.
  • Hold the door for ladies.

After the date, do NOT:

  • Suggest a nightcap in a hot tub.
  • Let anyone see you get on the bus or in your car if it is a beater.
  • Spoil the fact that you were fortunate to receive a phone number by texting something corny on the way home. 
  • Expect a marriage proposal.
  • Give up. Keep hitting that buffet, Babycakes.

Matchmaker, Matchmaker bake me a cake.

Do you have friends constantly trying to set you up? Have you tried online personals and dating services? Have you ever tried a matchmaking service? If you have, you know that none of these roads is likely to lead you to your soul mate, no matter what the ads and testimonials say. Your best bet is to get out there, get intoxicated, mingle, and have amnesia about rejection. It’s trial and error, my sweet: Mix, fail quickly, and mix again.

Still, I was curious so …

I did not meet with a matchmaker yesterday. She also didn’t do a silly thing like ask a writer not to write about the meeting that didn’t happen. She was cute (in my imagination) as she poked and prodded the defective merchandise (me) to see what his problem is.

Here are some typical questions that matchmakers ask (or, so I’ve heard) and answers that I might have given, if I were asked:

  1. Why love now? Why not? Who doesn’t love love? I could use more affection and sex and less manual labor, if you know what I mean. Still, I’m selfishly unwilling to change much about my lifestyle to accommodate a love monkey, just as I wouldn’t expect her to.
  2. Tell me about your most recent relationship and how it ended. We met in a bar, went on a few dates, and had almost-sex. Then the crazy texts, voice-mails, and emails ensued and I ran away like bear with his butt on fire. Now, I need to keep my head on a swivel when I’m looking for my next target so I’m not ambushed by yet another psycho ex.
  3. Where are you meeting most of the women you date? In a bar and, before you start lecturing me, I like bars. I’m not an alcoholic (denial is the first sign), but I find social lubrication a valuable resource to pull me from my shell and inspire my musings.
  4. Are you free of all baggage and ready for a serious relationship? Yes, I have no offspring, diseases, or jobs that require me to hop around the globe. I have two felines that are non-negotiable–all they do is sleep, eat, and shit anyway.
  5. What type of woman are you attracted to? The naked type. Ah, I kid. I am attracted to fit, intelligent, kind women. A sense of humor is absolutely necessary. There are obviously different degrees of each of these traits, which can offset or enhance others. For example, a funny woman who has a few extra pounds on her goes well with the few extra pounds I carry during the winter months. I’m not interested in having a woman with exposed ribs raise an eyebrow at my Pizookie* while she nibbles kale.

I hear that these matchmaking services can run from $2000 on up to $100,000. Holy shit! I bet many matchmakers will use the line, “You can’t put a price on love.” Yes, I can. Tonight, I shall employ a reliable (and silent) matchmaker by the name of Uppercut Cabernet. This fine specimen will cost me under $25 and cause increased cuteness with a chance of loving every time I tip it.

*Pizookie: It’s only the best fucking thing since peanut butter met chocolate. It’s a pizza cookie! You’re drooling right now, aren’t you? I know! It comes in a mini metal pan and a variety of cookie types from macadamia to chocolate chunk, it’s warm, and it’s topped with a scoop of ice cream. Go to BJ’s Restaurant and Brewhouse and try one. You’re welcome, fellow chubster.