Reconnected with ex's friend from college. Need advice.

Background: I (22M) recently reconnected with an old friend (22F) from college who I always thought was attractive but never pulled a move because I was dating another girl back then. I never intentionally got to know her as a friend but over the past year, I realized we shared a few similarities: playing tennis, traveling, being a foodie, and other things. We follow each other on IG and we'd always like each other's posts and be the one of the first to watch each other's stories. We also went to the same church and had lots of mutual friends, so when I broke up with my GF back then, everyone knew.

Current situation: Fast forward a few months after graduation, she moves to another city for work and I stay in town for grad school so IG was the only way to stay in touch. I heard that she broke up with her BF after graduation and I didn't pull a move until recently (last week): I replied to her IG story with a funny, teasing joke.

(For context, she posted a story about her "little" interns leaving her company. I replied with "there's only one little one here, are you leaving your company?? haha", where I was clearly teasing her about her height.)

Anyways, it was an amazing conversation starter and we've been talking for almost a week now nonstop. I asked about her job/transition into a new city while sending witty jokes based on her responses and it's been received quite well.

My intention is to get to know her a bit more as a friend since I never had a chance to do so during undergrad, but I realized I think I might have a small crush on her. I maintained daily communication responding ~ once a day with 3-4 messages after work hours to respect her time and space. At first, the conversation seemed one-way where I kept asking questions about her and her work, and there were many opportunities for her to reciprocate and ask me questions but she never did. Her responses were very open, genuine, fast (replies within < 30 min after sending my responses), and quite lengthy paragraphs which I took as a good sign. Another good sign: I mentioned how I recently finished grad school and just exploring my options for jobs, and without me asking, she offered to give me a referral at her company which is amazing!

I switched it up a bit and started asking deeper questions about her new church and her transition while mentioning that I also go to a new church now. She responds genuinely and openly AND she finally reciprocates by asking how my transition has been. Initially, I thought it was just her normal personality that made her not ask questions/reciprocate or that she wasn't interested in continuing the conversation BUT her responses remained deep and with breadth.

I then ask if she still stays in touch with people from our old church since most of them live in the same region she works at now, but she responds honestly with how it's been rough keeping in contact since no one responds and how post-college is just different. She also mentions how she's made a few friends at her new church. I respond by telling her my experience with the new transition and how it's been great, how life, in general, (despite the many transitions) has been amazing, and that I'm visiting NY later this month (I planted this "seed" to ask about her recent NY experience for a later convo). I also made a slight joke about how her transition seems a little "lonely" just to see how she'd react to the tease and see if it'd be reciprocated back.

Now: I'm simply waiting for her response. She sounds very genuine and very friendly, and I really want to get to know her a lot more without being too clingy/too obvious that I have a crush on her. My question is: is this headed in a good direction? Am I playing this cool and not too assertive? Is there anything I could do better? How do I gradually escape the friendzone?

TL;DR: Reconnected with ex's friend from college and we've been talking for almost a week with great rapport and good signs. What can I do better? Is this in the right direction if I'm interested in her and want to get to know her better? How do I gradually escape the friendzone?

Submitted August 16, 2019 at 10:58PM

Background: I (22M) recently reconnected with an old friend (22F) from college who I always thought was attractive but never pulled a move because I was dating another girl back then. I never intentionally got to know her as a friend but over the past year, I realized we shared a few similarities: playing tennis, traveling, being a foodie, and other things. We follow each other on IG and we'd always like each other's posts and be the one of the first to watch each other's stories. We also went to the same church and had lots of mutual friends, so when I broke up with my GF back then, everyone knew.Current situation: Fast forward a few months after graduation, she moves to another city for work and I stay in town for grad school so IG was the only way to stay in touch. I heard that she broke up with her BF after graduation and I didn't pull a move until recently (last week): I replied to her IG story with a funny, teasing joke.(For context, she posted a story about her "little" interns leaving her company. I replied with "there's only one little one here, are you leaving your company?? haha", where I was clearly teasing her about her height.)Anyways, it was an amazing conversation starter and we've been talking for almost a week now nonstop. I asked about her job/transition into a new city while sending witty jokes based on her responses and it's been received quite well.My intention is to get to know her a bit more as a friend since I never had a chance to do so during undergrad, but I realized I think I might have a small crush on her. I maintained daily communication responding ~ once a day with 3-4 messages after work hours to respect her time and space. At first, the conversation seemed one-way where I kept asking questions about her and her work, and there were many opportunities for her to reciprocate and ask me questions but she never did. Her responses were very open, genuine, fast (replies within < 30 min after sending my responses), and quite lengthy paragraphs which I took as a good sign. Another good sign: I mentioned how I recently finished grad school and just exploring my options for jobs, and without me asking, she offered to give me a referral at her company which is amazing!I switched it up a bit and started asking deeper questions about her new church and her transition while mentioning that I also go to a new church now. She responds genuinely and openly AND she finally reciprocates by asking how my transition has been. Initially, I thought it was just her normal personality that made her not ask questions/reciprocate or that she wasn't interested in continuing the conversation BUT her responses remained deep and with breadth.I then ask if she still stays in touch with people from our old church since most of them live in the same region she works at now, but she responds honestly with how it's been rough keeping in contact since no one responds and how post-college is just different. She also mentions how she's made a few friends at her new church. I respond by telling her my experience with the new transition and how it's been great, how life, in general, (despite the many transitions) has been amazing, and that I'm visiting NY later this month (I planted this "seed" to ask about her recent NY experience for a later convo). I also made a slight joke about how her transition seems a little "lonely" just to see how she'd react to the tease and see if it'd be reciprocated back.Now: I'm simply waiting for her response. She sounds very genuine and very friendly, and I really want to get to know her a lot more without being too clingy/too obvious that I have a crush on her. My question is: is this headed in a good direction? Am I playing this cool and not too assertive? Is there anything I could do better? How do I gradually escape the friendzone?TL;DR: Reconnected with ex's friend from college and we've been talking for almost a week with great rapport and good signs. What can I do better? Is this in the right direction if I'm interested in her and want to get to know her better? How do I gradually escape the friendzone?