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.

Outrageous First Dates: Verse One

Since discovering the opposite sex nearly two decades ago, I’ve had my fair share of memorable first dates -- from the sublime to the sublimely ridiculous. When it comes to the latter, I can’t help chuckling about some of the characters I’ve spent an evening with.

There was the NYC restaurateur who asked me if I wanted to hear about his broken engagement. In an effort to be polite, I hesitantly said yes--and then nothing more, as my date subjected me to a 30-minute retrospective of where he and his ex went wrong.

Then there was the Match.com guy who couldn’t seem to decide whether he was projecting too far into the past or the future. He remarked how cute our nicknames would sound together if we became a couple -- an observation that seemed a bit odd considering that it followed a lengthy exposition about his sex life with a previous girlfriend.

No roundup of outrageous first dates would be complete without mentioning my encounter with H, an ex’s best friend. Though said encounter wasn’t actually a date per se -- I had invited H to a singles party at my place -- it quickly became apparent he interpreted it as such.

After the soiree ended and it was just the two of us in the living room, I excused myself to go to the bathroom. When I returned, I found H stretched out across my bed (covers turned down, candles lit) naked as a jaybird. The unexpected dorsal view of a 6”3 guy was enough to shake me out of my slightly tipsy state. I made it clear that his little seduction routine wasn’t going anywhere, and instructed him to get dressed and go.

Funnily enough, though the outcome was exactly the same, this wasn’t my first experience of such forward first date behavior.

Stay tuned for more about that particular episode…and many more outrageous first date stories, including some from a few brave souls who’ve shared their own sordid tales with me.