Wayne & Wanda: I’m in Anchorage, my colleague is in Fairbanks. How can I tactfully ask her out?

Dear Wayne and Wanda,

I work with “Michelle.” We’ve gotten to know each other pretty well over the past few months, and I’m really attracted to her. We’re part of the same big team and colleagues – meaning it’s not like she’s my boss or vice versa. She’s smart, funny, and we get along great. I’m always happy when we collaborate on a project because her work is amazing. It sounds cheesy, but we really inspire each other. I think there’s a chance she’s interested in me too, but here’s the catch: I’m in Anchorage, she’s in Fairbanks.

I’ve been thinking back and forth about how to approach this. On the one hand, I don’t want to seem too pushy or make things awkward by suggesting that we travel to her place when we’re not together. On the other hand, I don’t want to miss the chance to get to know her better outside of work.

What do you think is the best way to ask her out without putting pressure on her or making her uncomfortable? Should I suggest a virtual date first, like a video chat over coffee or other drinks? Or do you think it would be better to keep it casual and perhaps suggest we meet up when she’s in town or when I’m in her town for work or another reason?

I guess what I’m really asking is: how do I go about this in a way that respects her boundaries (and I have no idea what those are) but also shows her that I’m genuinely interested in getting to know her better? I appreciate any advice you can give me. Navigating this new territory is a little daunting, but I really don’t want to let this opportunity pass without at least trying. I’m not the most experienced when it comes to dating. For me, career has always come first, so I look forward to hearing your thoughts.

Wanda says:

Anchorage to Fairbanks, eh? What’s 359 miles between friends and possibly more than friends? To be more specific, that’s over six hours of driving, or a few miles of Alaska Airlines and a few hours of combined airports and flight times. Heck, I rarely drive south of Tudor Road unless I’m leaving town, so I get it. Distance can be daunting, especially when seeking out a potential new connection.

However, let’s say you’re correctly assessing the mood in the room and Michelle likes you too. She’s probably wondering the same thing you are. How can I spend time with you when you live hundreds of miles apart? How can I initiate a meeting without freaking you out or invading your work boundaries? And what are your work boundaries? And do you like them too? Someone has to make the move here. Start, it’s your turn.

Personally, I think a virtual date sounds super weird. You might as well make it an agenda item after a staff meeting, you know? Since you both travel between cities for work, the next time you’re both in the same place, consider asking her to join you for drinks after work—or dinner, or coffee—just something that’s just the two of you.

You worry too much about that easy first date because you don’t live in the same city. But it’s no different than asking a coworker who lives down the street out. The only difference is that if it goes well, you’ll experience the adventure of a long-distance relationship.

Wayne says:

Ah, love in the Golden Heart City… I’m feeling all tingly. Oh wait, those are my ice cold extremities! Dip me in the hot springs ASAP!

OK, this isn’t business, this is personal, so stop sitting at your laptop waiting for her to send you a heart emoji at a witty pun in Teams chat, and get your lovesick butt up north for a long weekend to check the temperature—her feelings toward you—and the inland weather forecast so you can pack and dress accordingly.

Plan your trip as if she wasn’t going to be there, because that could happen. Rent a car and a room, set up a schedule of activities that fit your style and the time of year: museum, hot springs, northern lights and skiing, midnight sun and hiking, downtown parties and a boat ride on the Chena, whatever. Then, when you’re all set, tell her you’re coming to town in a few weeks and would love to hear from her about your itinerary and if there’s anything important missing… and that you’d also love to take her out to dinner at a place of her choosing so you can catch up.

This is an easy way to start a non-work-related conversation, and you’ll probably get a very good idea of ​​her reaction, too. She might want to rewrite your entire trip and play tour guide; she might come up with an excuse that she has to send out her dog team and completely snub you; she might meet you somewhere along the way and invite you to coffee or lunch. You won’t know until you take the action and ask. You’ll be relieved to finally take your chance, get some clarity on her interest, and have a good time in the land of midnight fun, whatever she decides.

(Wayne and Wanda: The date was great, but was it business or pleasure?)

(Wayne and Wanda: My budding romance was a fantasy. How can I make it a reality?)

(Wayne and Wanda: The talkative and flirtatious behavior of my colleagues drives me up)

(Ask Sahaj: I don’t want advice from my boyfriend who has never been in a relationship)

(Wayne and Wanda: The person I’m dating lets her out-of-control dog run free without a leash and it’s driving me crazy)