Category: Check him out before going out

  • “Tell me about yourself”

    The first real-time contact with a potential date can be awkward. You may have a sketchy description from an online profile, or just a few minutes of information from the friend who connected you. You want to find out more about him, but you’re not sure how to ask without seeming like you’re interrogating. So […]

  • Virtually falling for a guy

    I mean “virtually” two ways: As the dictionary defines it: “nearly, almost” as in not really; and Via the computer and/or phone; not face to face. My neighbor and I were once again comparing dating notes. She’s dipped her toe in the dating water a bit the last 6 months, going out with a handful […]

  • Think of dating like the movie “Groundhog Day”

    Remember the hilarious 1993 film “Groundhog Day”? Poor Bill Murray‘s character, Phil Connors, repeats the same day — Feb. 2, Groundhog Day — over and over and over again. But he’s aware that he’s reliving it so he begins to do different things each day, at first hedonistically, then he begins to reexamine his life […]

  • Phone number screens dating callers for you

    My friend Doug alerted me to a new service he thought would be perfect for daters (no, he’s not representing the company). It’s called It allows you to have a free phone number in any area code you want. You can give it to guys you meet online or in person and there’s no […]

  • Dating’s “pre-game” activities

    Have you been inundated with the Super Bowl pre-game activity options? You could easily devote the whole weekend to Super Bowl shows if you wanted. In scanning the various proceeding, it reminded me of a conversation I had recently with a single gal pal. We were talking about how important first impressions are in dating. […]

  • “I want to court you”

    These words are heart melting to a woman who wants love, romance, and a long-term relationship. No other man had said these to me. They were voiced after two weeks of nightly talking for hours about things that were important to each of us. What broke up past relationships, what was important to each of […]

  • Judging a guy by how well he … punctuates

    I was chatting with my friend Jeff Rubin (The Newsletter Guy) about dating profiles and punctuation today. “Punctuation?” you ask. “That’s a weird topic.” Not to Jeff and other of my friends. You see, Jeff started National Punctuation Day (Sept. 24) to call attention to the importance of proper punctuation. The book Eats, Shoots & […]

  • Dear Fido

    This guy kept coming to the top of my matches on one of the dating sites, so after a few months I decided to initiate contact. But I did so with his dog mentioned in his profile, which we’ll call “Fido” to protect his — and his owner’s — identity. The things mentioned are references […]

  • Be creative to get his attention!

    Last week I had two sublime dates, Wed. and Thurs., with a new guy (#65 if you’re keeping track). I loved being with him, and from all he said and did, it seemed he felt similarly. He called twice Friday while on a business trip (yes, even over a weekend). He’d said it was fine […]

  • Guy needs to make effort for first encounter

    I broke my own rule the other day — I initiated contact with a guy. I don’t know why I do this — the results are almost laughably predictable. He had looked at my profile, but didn’t write. I thought he was cute, smart, articulate, so I wrote. His response: “I live close to [intersection […]

  • Are you putting your best voice forward?

    Do you know what your voice projects about you to your potential date? Most people don’t. They can’t even stand to listen to their outgoing voice mail. But in the dating game, how you sound is one component of the dance that can either lead the guy to ask you out or beg off. Today […]