Bit of a long read so apologies in advance. Okay so for the sake of anonymity let's call this friend Sarah. Sarah and I went to high school together, and in our first year Sarah was infatuated with me and told me she loved me, however the feelings were not mutual at the time. We were on and off as friends thereafter, and in our senior high school years had periods of being very close and spending a lot of time during study breaks in the library together. There was a brief period where we were both single and somewhat romantic (held hands on the bus only) but otherwise we both had other long term partners.

Fast forward to now, after not having spoken for many years, we have been messaging for half a year or so and have caught up a few times for a meal or a few drinks. We get along well and both have done well for ourselves in life. In these catch ups we've discussed the dating sphere and how much it sucks, and have shared stories of some of our recent catastrophic first dates we've been on. We've both shared an interest in finding companionship. There has been plentiful laughter and eye contact during the times we've caught up. I find Sarah attractive and very compelling, and would certainly be interested in trying out a relationship.

In a recent (online) conversation, I said something along the lines of "well worst case if all else fails we have that pact we made in school of getting together if we're still single in our mid 30s" to which she jokingly responded by saying it's a bit of a cop out to call it the worst case. This was followed on by me jokingly saying there may be some disappointment from our peers at our school reunion if we ended up together (I was a bit of a bad boy at school and not liked by some, and she was a straight A saint) to which she responded by saying that wouldn't be the case, and many of the people from our grade she's told about us being in contact and catching up of late aren't surprised/disappointed. I'm yet to respond to her.

My question is, how would I go about this now? Do I just continue to catch up with Sarah in person and wait for things to possibly turn romantic organically? Do I take this opportunity in response to her in asking whether she would be interested in giving things a shot now and not in our mid 30s? And if so, what would be the best way to ask? I feel as though the delivery of how I ask may influence the outcome.

If anyone else has been in a situation like this before, your advice would be greatly appreciated!