Jenna,

I was on a first date with a girl I met at the racquet club. We met for dinner and ate outside in NYC at one of my favorite restaurants. It’s an amazing Italian cafe in Soho. Dark, small cobblestone streets, candlelight and amazing Southern Italian food. It was about 60 degrees outside with what felt like a warm summer breeze. One of those t-shirt and shorts days/jeans and sweater at night.

All of a sudden I got the song “Boys of Summer” in my head by Don Henley. It felt like a whisper from childhood, sweet summer days, first crush, broken heart, friends you’ll never see again. Although I really didn't know this girl I felt a major connection. Jenna, I think this might be the one. She makes me feel just amazing, Should I tell her how I felt that night or is this too much too soon. I don’t want to seem crazy. It’s just this is the first time in a while a girl has made me feel this way.



James K Manhattan, NY


James,

Call the clinic. “Boys of Summer” came into your head while you were eating with this young lady? Visions of “Black Snake Moan” popped into my head when reading this email.


Seriously, you sound like a sentimental guy, and there is obviously no problem with that – girls are always trying to curb a man’s false bravado – but you’ve got to tone it down a little. If she begins expressing similar feelings, feel free to let the cat out of the bag, but if you start tossing around big words like “Don Henley” it’s libel to scare her off.

It’s great you feel so strongly about her, but let her know in subtle ways, like bringing her lunch at work or surprising her with tickets to her favorite event. You said yourself that this is the first time in a while a girl has made you feel this way, so chances are you may have to nurse the relationship until the feelings are reciprocal.

Best,

Jenna

BOYS OF SUMMER

Jenna,

I have a date tonight. I met this girl who reminds me of a young Stevie Nicks. The problem is, she’s from one of those towns in Connecticut where people look at my 2005 Honda Accord like it’s a maroon 1987 Cutlass Supreme.

I think I’ve thrown together a nice outfit, some Nantucket reds (are they still in?), a classy sweater, but when it comes to foot apparel, I’m really leaning towards sandals. I know it’s winter, but my closet consists of the sandals and some old kangaroos?

Amulet Springer IIII
Middle Class Connecticut

Amulet,

Judging by your name, you shouldn’t need any advice in dealing with Connecticut’s old-boy upper crust, but here’s the deal: I could tell you love should be blind to any of these trivial details, but sometimes it takes a little superficiality – and a little style – to get in to the heart of such a woman.

Your reds will be fine, but neither the Kangaroos nor the sandals are going to sweep this girl off her feet. Both, however, may intrigue her. If you can wow her with your conversation, choice of restaurant, etc, then she will see this faux-pah as quirky and cute.

If forced to choose, I would go sandals and make sure to walk through a few icy puddles without a flinch – regardless of how proper this dame may be, every girl wants a little bad ass in their man. Walking through a frigid puddle isn’t the same as say, saving her from a couple of violent muggers, but she might notice it and give you a place to warm those puppies up later on.

Best of Luck,
Jenna