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Dinner With Cupid

Hitting the slopes

Will this blind date end with black diamonds or hearts?

From left, Alison Webb and Tim Maclean.

From left, Alison Webb and Tim Maclean.

TIM MACLEAN

34 / ENGINEER FOR KEURIG

HIS IDEA OF A PERFECT SATURDAY

Waking up to a surprise foot of snow and hitting the mountains to ski the fresh lines all day

WHO PLAYS HIM IN THE MOVIE ON HIS LIFE?

Matt Damon

ALISON WEBB

Continue reading below

28 / CONSULTANT

HER IDEA OF A PERFECT SATURDAY

In winter, downhill skiing followed by cross-country skiing with the dog and recovering in front of a wood fire

WHO PLAYS HER IN THE MOVIE ON HER LIFE?

Jennifer Lawrence

7 P.M. PARK RESTAURANT & BAR, CAMBRIDGE

> UP THE GONDOLA

ALISON I actually had no time to prepare. I was just praying I’d be on time because I had two conference calls run later than expected.

TIM I arrived first and was shown to the table.

ALISON I was a little nervous but mostly excited to meet someone completely new.

TIM She was cute. Keeps herself in good shape.

ALISON Tim is a good-looking guy and greeted me with a nice smile and confident stance.

TIM We talked about our weekends; it turns out we were both skiing at the same place.

ALISON Within a minute, we realized we both ski at Killington, so that broke the ice very quickly.

TIM I was calm, rather curious what I was getting myself into.

ALISON Skiing . . . was a real icebreaker, which led to a lot of other topics outside of the normal “where do you work, live, [where did you go to] school” and the name game, which can get really boring. The vibe in the restaurant was cool, and I’d recommend it to friends.

> THE TRAVERSE

ALISON The waiter was patient. We weren’t ready the first few times he came by because we kept forgetting to look at the menu.

TIM There is a good chance we’ve crossed paths before and didn’t know it.

ALISON We have a ton in common — skiing, travel, core values, engineering degrees, and his former employer is one of my biggest clients.

TIM We talked a little about our jobs but mostly kept to the fun stuff and left work at the office.

ALISON My attraction grew as I learned how much we have in common. It seemed like we could easily spend hours together.

ALISON I was relatively comfortable from the start and stayed comfortable throughout the evening.

>APRESSKI

TIM It was a school night, so we had to work in the morning.

ALISON No nightcap this time. I left looking forward to seeing him on the hill and at happy hour in Killington.

TIM We exchanged numbers and gave each other a good-night hug.

ALISON Who wants to make out in a concrete parking lot! I did wonder if we are better suited as friends first and maybe more down the road.

> A SECOND DATE?

TIM We may see each other on the slopes.

ALISON Yes. Ski date.

TIM B

ALISON A

 — Compiled by Alex Stills

GO ON A BLIND DATE. WE’LL PICK UP THE TAB. Fill out an application at boston.com/cupid.

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