A weekly series in which our expert in all things everything solves life’s conundrums, big and small.  Got a problem that could use a no-nonsense perspective?  Tell it to the Co-It-All at voice@intheco.com

Dear Co-It-All,  

I started dating a new girl one month ago. Things are going really well—we text most days and see each other a couple times a week. Still, we haven’t had any discussions about whether we’re an official “couple” yet. Any thoughts on the perfect Valentines gift for this in-between stage?

Here’s a thought: Never start dating someone new in January, because Valentines Day and new relationships go together like Coldplay and The Super Bowl. Meaning that they don’t go together at all, and when you force them together, things can get pretty embarrassing, pretty quickly. The good news: It’s unlikely that Beyoncé will arrive to upstage the hell out of your awkward V-Day celebration. The bad news: It’s unlikely that Beyoncé will arrive to upstage the hell out of your awkward V-Day celebration.

Seriously though—this conundrum is as common as they come: A lot of new romances bloom over the booze-laden holiday season, and many more when singletons resolve to put themselves “out there” in the new year. And then you blink and all of a sudden it’s February and along comes a holiday devoted to cheesy declarations of eternal devotion. Don’t get me wrong. For long-established couples, hearts day can be a good excuse to dust off ye olde flames of passion (read: get out of your adult onesie and make dinner plans that don’t involve your smart phone and the Uber Eats app).

For new and newish couples though, it’s a minefield of potential missteps: Too little effort and you run the risk of looking like a disinterested jerk, but too much effort, and suddenly you’re the guy standing outside of her window holding a boom box over your head.


It’s not fair, really, that we live in a world where quote/unquote “coolness” and making an effort are somehow deemed to be at odds with each other. This (sad, but true) reality tends to go double for dudes in straight relationships. Yes, we women want to end up with a sensitive soul mate who will give foot massages and watch The Bachelor with us when we’re sick. But first we want to lust after a guy who keeps his emotional cards close to his chest. So if by chance your inner Don Juan is telling you to decorate her bedroom in rose petals or recite an original poem—ignore him. Or at least tell him to crank it down a notch.

So what are some gifts that will elicit the exact right amount of awwwww (without even a trace of ewwwww)? That’s a tricky one given that that I have never met your not-yet-gf, and have zero idea of her tastes. What about tickets to a concert (or a play or a lecture or a monster tuck rally)? That definitely veers away from any Hallmark heinousness of the holiday. Plus, tickets to a future event are a great way of demonstrating that you think this relationship is going somewhere, without saddling your V-Day with the whole “where is this relationship going?” convo.

Other options could include making a reservation at a restaurant she has mentioned, a book or an album that has some kind of significance to the two of you, a gift certificate for a massage (assuming she likes that sort of thing) or a nice bottle of wine that you can enjoy together…unless that is something she would find pretentious and off putting.

Valentines is on a Sunday this year, so maybe it’s just a matter of planning a fun day together—brunch, followed by ice skating or basket weaving or axe throwing. It’s less about what you actually do and more about showing that you actually care.

You’ll notice that all of my suggestions lean towards the experiential. I feel like those gifts are the most memorable and also—doesn’t everybody have enough crap in their lives?

For that reason (and for many others), I would avoid clothing. I would also avoid clothing that goes under clothing (read: sexy lingerie) because you are not a sugar daddy, teddy bears (because she is not seven), beauty or grooming products (because that’s just offensive), jewelry (because—whoa—slow down!!), and boxes of chocolate…because only a few are ever any good, and then she’s left with a box of rum raisin and marzipan-flavoured crap…which she will eventually eat when she’s craving something sweet…and then she will resent you for it.

Not sure if any of this has solved your problem, but hopefully you’re feeling less anxiety over what is really not that big of a deal. Try to think of the holiday as an opportunity to solidify an already good thing, rather than a make or break scenario. If you end up together, a bad gift will be something you can joke about for years to come. And if you don’t, well, she’ll just be that random girl who you once took to a basket weaving class. No biggie.