The text messages had sparked up again, his intent still anything but clear - an attempt to be friends, an appeal for advice (why mine?), the proposing of a date or merely gaging my interest? My patience was up.
Simplicity seemed elusive in my own dating life and in those of my friends. But still, on a rooftop bar one Sunday evening, the questions continued.
"Maybe things are different now" I ventured, aware that the last people willing to call themselves my boyfriend slunk away in 2008 and 2011; the carefree days of my early to mid twenties. Who could say what issues beset the relationship landscape two years on?
The Shard winked at us from across the city, and we winced at the sunshine and the prices next to each drink on the menu.
"I don't know." I continued. "Maybe once you get to your late 20s, 30s and beyond, things just aren't as straight forward any more."
It was a conclusion that had come while recounting my own confusion and listening to the stories of others: tales where ambiguity, intense feelings, and a very apparent fear of commitment seemed to be recurring themes.
But through it all, a thought remained: if things aren't still as simple as two people wanting to be with each other now, end of - when you're childless, mortgage-less and haven't got ceremonies and certificates binding you together - when will they be? Is that too idealistic, or do we really need to be giving these problem-boys a chance?
These days it seems like we're stuck on conundrums that weren't there before: do we waste time working at something, or accept the signs and move on? Or in real terms, if a thirty year old man still communicates in riddles and emoticons now, is it worth sticking around and hoping he'll grow out of it?
The cocktails arrived and we took a sip each. A beautiful girl opposite was crying into her Mojito, and our own drinks sweated onto the glass table while London stretched out around us.
"Well, part of me doesn't want to give up on the relationship, because we clearly have something. And part of me doesn't want to waste any more time if it's not going anywhere." my friend said with a sigh.
"I get that, but still think it should be an easy choice to make - whether you want to be with someone or not - at least to begin with. Anyway, I'm hardly one to talk. Maybe this is just how it is."
We sat in contemplative silence and she slipped off to the toilet. I flicked through my own puzzle of text messages, yep - still confused, and then checked my email inbox.
One message received, it read. An old colleague continuing a brief, lighthearted conversation from a day or two before.
Well anyway, when you get back from holiday - would you like to go for a drink?
Or perhaps, I thought, sending a response in the affirmative along with my phone number, there's a chance things could still be simple after all.