When He Doesn't Take The Hint

It's great when a man takes some initiative about pursuing you. It’s decidedly less appealing, though, when you’re not interested – a fact of which I was reminded recently with two different guys.

First, there was JDate.com member Scott. Prior to our long-delayed second date, I communicated very clearly that I’m not a fan of last-minute plans. After date #2, I received the following text message from him:

“Hey cutie, want to watch a football game tonight at ur place free massage included and btw I’m the best! Xo”

Turned off by his forwardness (not to mention bad grammar), I declined Scott’s invitation. The next day, he followed up with—

“Football tonight? And a spa massage xo”

Equally persistent was the New Jersey resident whom I politely but firmly told by email that I had no romantic feelings for. He said he would like to remain friends, so I invited him to my recent singles party.

He proceeded to suggest (multiple times) that I come to his hometown -- 2 hours from NYC -- so that we could work out together. At the party, I was happily flirting with another guy when Mr. New Jersey sauntered over. He put his arm around me and exclaimed—

“I think you’re just the bomb!”

Talk about a conversation killer. Though Mr. NJ nixed my opportunity with the other guy, he managed to teach me a valuable lesson – when a guy doesn’t seem to be taking the hint that you’re not into him, leave him off of your guest list.

Coming up…a first date raises a big question and a charitable night out with Whoopi Goldberg.

Musing About May-December Love

When it comes to May-December romance, I’m about as intimately acquainted with it as Mr. and Mrs. Kutcher.

Ashton and Demi: the poster couple for May-December love

My first two boyfriends were 16 years older than me. And my late and much-loved parents (who adored each other) had a 25-year age difference between them.

For as much, though, as I’ve always been and continue to be drawn to older men, I know the May-December dynamic isn’t for everyone. And that in some cases, it’s downright creepy.

Take, for example, the sixty year old guy who recently emailed my 25-year-old friend Diana through a dating site -- eight times. In his ninth attempt to make contact, he asked why she wasn't responding to his messages.

“Sorry,” she said politely. “I think our age difference is too steep and I'm just not interested. Thanks, though, and good luck!"

His response, as another friend of mine quipped, suggests he hasn’t dealt with rejection since the Reagan years--

“I'm surprised that someone who claims to be so sweet would make a nasty, gratuitous comment like that. A simple no would have been fine. That comment was very nasty for no reason. But I feel better as I never want to be with a mean person and that was, needlessly, mean. I bet I still see your [profile] for a long time.”

I guess even among the AARP set, ettiquette is fleeting in cyberspace.

Up next…drinks with a member of NY’s Finest and Single Gal In The City--the book?

Outrageous Online Dating Tales: Part Two

In the uncertain world of online dating, romantic chemistry isn’t always easy to find. Also increasingly rare – the art of handling rejection gracefully.

Last week, a good friend of mine forwarded me an email exchange with a JDate.com bachelor whom she didn’t feel any sparks with. She politely told him her feelings:

“It was lovely meeting you, though to be honest, I don't think we are a match. I appreciate your not playing games and being very up front - it's sweet and flattering. I know you'll make "the" girl very happy one day. Best of luck in the search.”

This was his grammatically challenged response:

“I guess you should have told me right after we wet for yogurt that you didn’t feel it..I would have saved blowing the additional $20 at the shrimp bar. I would have much rather given the money to some beggar. I try to be mentsch and a gentleman and treat a girl with class, and what I get in return is, as to be expected from women like you, a punch in the gut…

When you are 40, and still single, which I am certain you will still be (no offense, just being candid) you will look back and say: wow I can’t have any kids at this age and I am all alone. There were so many guys out there that were nice to me, but I had to play “Miss Big Shot” and pray that a shining knight on a white horse from Jdate no less, will sweep me off my find. Get real and good luck to you too!”

So much for being a gentleman.

Speaking of ungentlemanly behavior, the above email got me to thinking about one of my online dating horror stories with a guy from TheSquare.com.

Seconds after we met, he said I looked “different” from my profile photo – and that that was neither good or bad.

Upon returning home from our 10-minute date, I couldn’t resist the impulse to email him and say it’s impolite to insult someone straight off the bat. His reply—

“If I had told you what I really thought, you would’ve slapped me across the face.”

And this was from a man whose profile headline read, “Harry Seeking Sally.” Talk about false advertising.

Fortunately, online dating disasters like the above are occasionally balanced out by the unexpected good guy. Coming up…details about my recent encounter with a sweet bachelor in that category.