Dear Wayne and Wanda,

I work with “Michelle.” We’ve gotten to know each other pretty well over the past few months, and I’ve found myself really drawn to her. We are part of the same large team and peers — meaning, it’s not like she’s my supervisor, or vice versa. She’s smart, funny, and we get along great. I’m stoked every time we get to partner up on a project because her work is amazing, and it sounds cheesy but we really do inspire each other. I think there’s a possibility that she might be interested in me too, but here’s the catch: I’m in Anchorage, she’s in Fairbanks.

I’ve been going back and forth on how to approach this. On one hand, I don’t want to come off too strong or make things awkward by suggesting that I travel to see her when we’re not even dating. 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 making her feel pressured or uncomfortable? Should I suggest a virtual date first, like a video chat over coffee or drinks? Or do you think it would be better to keep it light and casual, maybe suggesting we meet up if she’s ever in town, or if I find myself in her city for work or another reason?

I guess what I’m really asking is: How do I move forward in a way that respects her boundaries (and I have no idea what those are), but also lets her know that I’m genuinely interested in getting to know her better? I appreciate any guidance you can offer. Navigating this new territory is a bit daunting, but I really don’t want to let this opportunity slip by without at least trying. I’m not the most experienced with dating. I’ve always put career first. So I’m looking forward to hearing your thoughts.

Wanda says:

Anchorage to Fairbanks, eh? What’s 359 miles between friends and potentially more-than-friends? To be specific, it’s a six-plus-hour drive or a chunk of Alaska Airlines miles 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 in navigating a potential new connection.

Let’s assume, though, that you’re reading the room accurately here, and Michelle likes you back. She’s probably wondering the same things you are. How to spend time with you when you live hundreds of miles apart? How to initiate a hangout without freaking you out or creeping in on work boundaries? And what are your work boundaries? And do you like her too? Someone has to make a move here. Tag, you’re it.

Personally, I think a virtual date sounds super awkward. Might as well make it an agenda item after a staff meeting, you know? Since you both apparently travel between cities for your jobs, target the next time you’re both in the same physical spot, and ask her to join you for drinks after work — or dinner, or coffee — just something that involves only the two of you.

You’re overthinking this simple first date because you don’t live in the same city. But it’s no different than asking out a co-worker who lives down the road. The only difference is, if it goes well, then you have the adventure of navigating a long-distance relationship.

Wayne says:

Ah, love in the Golden Heart City … makes me feel all tingly. Oh wait, that’s my freezing extremities! Dip me in the hot springs ASAP!

OK, this isn’t business, it’s personal, so stop sitting at your laptop and waiting for her to drop a heart emoji over a witty Teams chat pun and get your lovelorn butt up to the Far North for a long weekend to check the temperature — of her feelings about you and the Interior weather forecast so you can pack/dress appropriately.

Plan your trip as if she’s not going to be involved because she might not be. Rent a car and get a room, make a schedule of activities that fit your style and the season: the museum, hot springs, northern lights and skiing, Midnight Sun and hiking, downtown partying and floating the Chena, whatever. Then, when everything’s together, tell her that you’re coming to town in a few weeks and would love to get her advice on your itinerary and if anything critical is missing … and that you’d also love to take her out to dinner at a place of her choosing so you can catch up.

That’s an easy way to strike up a conversation that isn’t about work, and you’ll also likely get a very solid vibe check from her response. She might rewrite your entire trip and want to play tour guide; she might make up an excuse about having to run her dog team and shoot you down entirely; she might meet you somewhere in between and catch you for coffee or lunch. You won’t know until you act and ask. You’ll feel relief in finally shooting your shot, get some clarity on her interest, and have good times in the Land of the Midnight Fun no matter what she decides.

[Wayne and Wanda: The date was great, but was it business or pleasure?]

[Wayne and Wanda: My budding romance has been a fantasy. How do I bring it into reality?]

[Wayne and Wanda: My co-workers’ gossipy, flirty behavior is driving me up our cubicle walls]

[Ask Sahaj: I don’t want advice from my friend who’s never been in a relationship]

[Wayne and Wanda: The person I’m dating lets her out-of-control dog run wild off leash, and it drives me nuts]

Because I love to travel, there are a couple of exercises I perform each day. First, I do a quick glance at some of my favorite destinations to see if rates are going up or down. Then, I check the mailbox to see if credit card companies are sending any bonus offers if I get a new card.

If you look long enough and dig deep enough, you’re likely to find some really crazy deals. Mind you, some of the deals are really good. Others are really weird. Last week, I uncovered a couple of doozies.

Fares from Anchorage to Guatemala are pretty inexpensive to begin with. As Alaska Airlines ramped up service from Los Angeles, more travelers started taking a closer look at the country, just south of Mexico. Alaska Airlines competes with Delta, United and American Airlines on the route, so it’s a competitive market.

Avianca, one of the largest airlines in Central America, doesn’t fly all the way to Anchorage. But they’re offering a $99.30 one-way fare from Anchorage to Guatemala City. Avianca is part of the Star Alliance along with United and Lufthansa. But in this case, Avianca uses Alaska Airlines to fly travelers first to Los Angeles before they continue to Guatemala City.

There’s no advance purchase required to get this rate. Last time I checked (on Friday), seats were available on Aug. 25 and 26, Sept. 1, 6, 20, 24 and 27. Reservations are available on Avianca’s website.

Although it’s a really inexpensive flight, there’s a long layover in L.A. Flying on Sept. 6, the layover is almost 16 hours.

While the $99.30 one-way fare is a Basic Economy fare on Avianca, it’s booked in the main cabin on Alaska’s nonstop between Anchorage and Los Angeles. That means travelers receive full mileage credit (2,340 miles) and can request an assigned seat. Because the reservation must be made on Avianca’s website, you may have to call Alaska to get your seat assignment in advance.

This itinerary is a perfect example of a Skiplagged moment. That is, where an itinerary to a point beyond Los Angeles is significantly less than a ticket just to LA. A short-notice ticket on Alaska’s nonstop flight can cost more than $500 one-way.

Getting back from Guatemala to Anchorage on short notice is more expensive, but still affordable: $250-$300 one-way on either United or Alaska Airlines.

Plan ahead for next winter and get a cheap rate in both directions. The $99.30 one-way fare is available between Jan. 10 and March 9, 2025. The return flight, also with a lengthy layover in L.A., is $148 one-way between Jan. 9 and March 3, 2025.

If this seems like a good deal for you, make your reservations promptly. I was corresponding with one traveler about these rates and she asked, “How long do these deals usually last?”

I answered, “Not long.”

In fact, last night the same $99 fare was available from Anchorage to El Salvador’s international airport in San Salvador. That’s the country just south of Guatemala. But today, that bargain is gone.

[Best practices for trouble-free travel to the Lower 48]

If you still want to visit Europe via one of the seasonal nonstop flights, there’s a last-minute deal on Condor.

Fly nonstop from Anchorage on Thursday, Sept 5, returning on either Sept. 12 or 14. The price for an economy ticket is $510 round-trip. Just last week it was $550 round-trip and I thought that was a deal! Since Condor is a mileage partner with Alaska Airlines, you can earn 50% of the actual miles flown with Condor. For the return flight on either Sept. 12 or 14, it’s $190 one-way to upgrade to Premium class. There’s more legroom, a bigger luggage limit and nicer seats. Book this reservation at Condor’s website.

If you would rather redeem Alaska Airlines miles for your Condor flight, it’s 27,500 miles for the outbound flight on Sept. 5 to Frankfurt, plus $49 in fees. For the return flight, it’s also 27,500 Alaska Air miles for economy, or 35,000 for Premium. Add on $197 in fees. Book your mileage tickets on Alaska Air’s website.

On the credit card front, Alaska Airlines really wants you to have one or two Visa cards! On my flight back from Portland the other day, the flyer in the seat-back pocket boasted a 65,000-mile bonus if you paid the $95 fee and made the minimum spend ($3,000 charged within the first 90 days). The bonus amount changes from time to time — I’ve seen it as high as 70,000 miles. That will get you to Frankfurt and back, as long as you pay the $246 in fees.

I carry a couple of credit cards from Chase, because of its Ultimate Rewards program. Once you get your points, you can shift them to several different airlines or hotel companies, including Hyatt, Bonvoy (Sheraton and Marriott) or IHG (Holiday Inn and Intercontinental).

In the mail, I received an offer for the Ink Business Preferred card from Chase. What caught my eye was the 120,000-point bonus. To get this boatload of points, which is worth between $1,200-$1,500, you have to pay the fee of $95 and charge at least $8,000 in the first three months. That’s a lot of free nights at Hyatt Hotels.

Honestly, I’m still pondering whether I could come up with $8,000 in charges — but I’m seriously considering this card just to get the bonus points!

In addition to shifting the points to any number of airlines, you also can redeem the points at Chase’s travel service at the rate of a penny a point. That’s not a great exchange rate, but you could use your points to buy tickets at Alaska Airlines — and earn miles on your ticket.

Remember: All fares are subject to change without notice. And they change all the time.

[Travel: Who gets the airline miles in the divorce?]

Even by the adjusted standards of a non-general election, Alaska voters’ participation in last Tuesday’s primary was anemic. Several factors were at play, of course: Other than the high-profile U.S. House race between Rep. Mary Peltola, Nick Begich III and Lt. Gov. Nancy Dahlstrom, there were few major draws on the ballot — and even the House race lacked the high drama of 2022′s special primary, where dozens of candidates were whittled to just four, or its general election, where Alaskans selected a candidate not named Don Young to Alaska’s sole U.S. House seat for the first time in almost 50 years.

Most of all, though, the biggest contributor to the lackluster primary election turnout was likely its lack of serious consequences. In selecting a better method to elect candidates — ranked choice voting — Alaska has unintentionally removed most of the stakes and necessity of contests prior to the November general election.

Under the state’s open primary system, instituted by the same ballot measure that gave us RCV, Alaska voters select the candidate they like best in the primary, similar to the old system (but with all candidates on the same ballot), and the top four vote-getters in each race move on to the general election. But nearly all races except statewide ones have fewer than four candidates anyway, so the practical impact of the primary is nil. To be sure, there were a few races where the primary had a winnowing effect — in Eagle River’s Senate seat, for instance, former Rep. Sharon Jackson was the red-lantern finisher among five candidates and was thus knocked out. Similarly, in a wide-open race for House District 36 in the rural Interior, Libertarian candidate James Fields came in fifth and won’t be on the November ballot. And in the aforementioned U.S. House race, eight also-rans who cumulatively secured just more than 2% of the vote were eliminated. But those were the only races that were affected by the primary — a tiny fraction of the 51 total races on Alaska ballots.

Given the lack of paring-down in nearly all races, the principal utility that Alaska’s primary election has at this point is as a massive free poll for candidates and (if they have them) the parties that support them, giving them a sense of the state of the race three months before it’s actually contested. But the reality is that the data provided isn’t altogether predictive of future election returns — primary voters tend to be more motivated and more partisan than general election voters, so their preferences may not line up well with how things will go when the seats are decided. Other voters will be motivated to turn out in the general election by the presidential contest. And as RCV lets us rank all of the candidates who emerge, there’s less turnout incentive for primaries — even if a screwball or two ends up among the field, it’s a problem easily remedied by ranking other candidates higher. Sure, it’s interesting to see how people feel about the candidates in the race a few months out, but does that justify the expense of an entire election? If campaigns and parties want that information, it would make more sense for them to pay for polls rather than Alaskans doing the work (and shelling out public money to cover the cost) for them. Indeed, in some races — most notably the U.S. House race — we’ve seen candidates drop out in order to elevate a single candidate from one party. If the parties find utility here, we should be willing to ask ourselves: Should Alaskans fund an election just to help the parties get organized? The parties should fund and conduct that activity themselves if it’s useful for them.

There are a few edge cases where primaries would still have clear usefulness to Alaska voters — for instance, if candidate numbers skyrocketed to the point that ballots in November became unwieldy (say, if many races turned into the free-for-all of the 2022 U.S. House special primary), though that hardly seems likely. Even if six or seven candidates were on the general election ballot, ranking the top four would still easily decide elections, and it’s hard to imagine any race outcomes changing. Another low-likelihood scenario would be if bad actors registered candidates with similar names to a legitimate candidate in an attempt to confuse voters — but that’s a scenario that the status quo (or, for that matter, the old voting system) doesn’t guard against, either.

Alaska’s short history with ranked choice voting has so far been a strong success, giving candidates an incentive to consider the preferences of all their constituents, not just the party faithful. The system has been called “instant-runoff” voting because of the ability to consider voters’ second, third and fourth choices instantaneously. Now it’s increasingly looking like it might have the secondary benefit of removing the need for the state to pay for an additional statewide election every year.