Ask Dr. Nerdlove by Harris O'Malley

How Do I Ask A Friend Out On A Date?

DEAR DR. NERDLOVE: I’m finding that, throughout the pandemic, a lot of long-term couples have broken up – including a few mixed-orientation ones where I’ve known the woman for a while, but never imagined having the opportunity to ask out.

With the end of the pandemic (hopefully) near, and thinking they’re attractive and would make a good partner, what tips/suggestions would you offer someone thinking about approaching another person they’ve only ever known to be taken, and who’s likely never viewed them as someone they’d date?

– From Friends to More

DEAR FROM FRIENDS TO MORE: This is the sort of question that tends to engender a lot of strong feelings in folks, FFM, because a lot of folks have had people — mostly, but not exclusively men — who rolled up on them as soon as they broke up like the dude thought he’d just found the golden ticket while they were still reeling from dumping or having been dumped. It’s a really s--tty feeling, especially when it’s coming from someone they had thought of as a friend.

But let’s start with the assumption of good faith. You haven’t just been waiting around for your chance to get with the Newly Single and that there are new and previously unexpected feels. a

There’re a couple questions that need to be answered first.

First: how long ago did they break up? If someone just left a long-term relationship, especially under trying circumstances like, say, a global pandemic, they’ve probably got some s--t to work through first. While there’re plenty of times where people have gotten over their relationship while they were still in it, the odds are good that a fresh break up means that they’re going to be in mourning for what was and what might have been. Ending a long-term relationship often means being deep in your feels while you try to figure out who you are now and what you want to do next. Having someone roll up on them right away because the proverbial window is open can feel kind of insulting. It’s like that person was just waiting for their opportunity, rather than considering the needs and feelings of the person who just ended a relationship.

While there’s no hard and fast timeline for when someone will be ready to date again, the closer they are to the break-up, the less likely they are to appreciate being asked out on a date. However, they are the ultimate arbiters of whether they’re ready to date again or not… and they may well discover that they aren’t. Or they may be ready to go a little wild, but not want to date. They’re the ones who’ll have to take the lead in terms of what, precisely, they’re up for at that moment.

Second: is there actual, mutual chemistry between the two of you? One of the keys to moving from platonic friends to something more is that there needs to be attraction that’s goes both ways. If you and they haven’t had a flirty thing beforehand, then you should make sure that there’s some actual interest. Very light flirting can serve as a means of pinging for interest; if they flirt back, then the odds are better that they might be more receptive to an actual date. If not… well, probably best to let things be. Flirting also can serve as a low-stakes way of signaling that you’re interested, but without putting them in the awkward position of having to acknowledge it directly. If you’re just a little flirty and they’re not interested, they have the option of ignoring it or pretending they didn’t pick up on the vibe you were putting out there. That way, you can save face (she didn’t pick up on it) while she doesn’t have to deal with the awkwardness of having to say “thanks but no”, and the two of you can have the silent agreement to shove that moment down the memory hole and act like it never happened.

Third: if they are ready to date and you’re pretty sure you’re picking up mutual interest, invite the “no”. If you ask them out on a date, make it clear in advance that you’re cool if they aren’t feeling it. You want to say something along the lines of “Hey, I want to ask you something and it’s totally cool to tell me no. You’re an awesome person and I really value our friendship, but I like you as more than a friend and I’d like to take you out on an actual date.” Inviting the no helps defuse the awkwardness because you’re letting them know that you realize it’s a bit of an ask and that they may feel weird about having to turn you down. It can serve as a pressure release valve of sorts, so they don’t feel like they have to give you a soft no or to stall for time and then turn you down later on… which would end up being even more awkward in the long term.

Giving them that out and letting them know you’re ok with them taking it means that, even if they do say no, you may not get the date, but you will be able to keep your friendship.

And, incidentally, there’s one more thing to consider: part of why making the leap from friends to lovers can be difficult is because a lot of times, your friend has only seen you as a friend. If you haven’t expressed interest and the two of you haven’t had chemistry before, your asking her out will likely feel like it’s coming out of the clear blue sky and forcing her to reconsider and recontextualize how she sees you and the nature of your friendship. It’s a little easier if you can hit that cosmic reset button that causes her to see you in a different light — a long time apart, a major change, and so on. Otherwise, the inertia of friendship can be difficult to overcome, even if she feels like she should be attracted to you… but isn’t.

Good luck.

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