Looking for an objective third-party perspective on a coworker I started dating

[Anonymous]

 

I'm looking for some outside perspective on a situation with a woman I used to work with. I'm interested in her romantically, but I'm not sure how much of that interest is reciprocated. I'd appreciate honest advice, including if you think I'm reading too much into things.

I've tried to keep this chronological and distinguish what happened from my interpretation.

Background

We used to work at the same grocery-related retail location. She's relatively shy, and I'm also shy and introverted, especially around people I don't know well.

For a long time, we didn't talk much. I occasionally approached her, but over time she started approaching me more often, usually with a joke or a question that wasn't necessarily work-related.

I noticed that she seemed more likely to initiate these interactions when I was alone or away from other coworkers. We gradually started talking more regularly, probably over the last month or two that we worked together.

She transferred to another store around the time we started communicating more. The transfer was partly related to work scheduling and staffing, and she has since been moved around between locations. Her work situation has been pretty chaotic.

I don't know exactly how she got my phone number. I never directly gave it to her. We have mutual coworkers, and it may have come from a work group text or someone we both know.

How we started texting

Around the middle of October, she texted me for the first time about something work-related. It was a practical message about something she had forgotten at work.

We then exchanged a few messages about a shirt she had left behind.

After that, our conversations gradually became more frequent and less work-related.

We started talking about things like:

Work frustrations and coworkers.

Cars, repairs, and working on vehicles.

Gaming and PC hardware.

Pets and funny things they do.

Food and cooking.

Family and childhood stories.

Holidays and traditions.

Random jokes and memes.

Our texting style is pretty sarcastic and playful. We joke around and occasionally tease each other. In the beginning I sent the longer messages and carried more of the conversation.

However, she also contributes her own topics and stories. She has talked about her family, her interests, her apartment, her car, and things happening in her life without me necessarily asking about those specific subjects.

She also sometimes initiates conversations or sends something that gives us a new topic to discuss.

We developed a few inside jokes, including jokingly calling each other names related to being overweight. She seems comfortable with that humor, and it has become part of our conversations.

The first invitation

On October 19, I asked her if she wanted to go to one of several Halloween events with me.

I specifically said I was planning to go to one before Halloween was over and asked if she'd like to come.

She responded enthusiastically, saying it sounded fun and that she was fine with whichever event I wanted to do.

She helped choose a date that worked for her.

We decided to go to a Halloween attraction with haunted houses and carnival rides.

I offered to buy the tickets and suggested either meeting there or carpooling. We decided carpooling would be easier.

She gave me her address, completed the event waiver, and we arranged a pickup time.

At this point, I wasn't sure whether she interpreted the invitation as a date or as a friendly outing.

I hadn't explicitly called it a date.

The first outing

We went to the Halloween event together.

We spent time going through the haunted houses, riding some carnival rides, and walking around.

During one of the haunted houses, I offered her my arm, and she took it.

We had playful banter throughout the evening, and I made her laugh several times.

At one point, we sat together on haybales and talked for a while.

We also spent some time talking in my truck near her apartment before I left.

One thing that stood out was that we went into the gift shop and picked out a shirt. She picked out the same shirt for me so we could match.

I thought that was a cute and playful gesture, although I don't know whether it meant anything romantic.

Overall, I felt like she enjoyed herself.

I didn't try to kiss her or initiate anything beyond offering my arm during the haunted house.

I wasn't sure whether that was the right opportunity to make any kind of move, and I didn't want to make her uncomfortable as she is shy.

After the first outing

We continued texting afterward.

She mentioned that she was wearing the shirt we picked out together and said it was comfortable.

We continued joking around and talking about various things.

She also shared more about her life, including her interest in cars, her family, her apartment, and her work situation.

Her schedule became increasingly chaotic because of transfers between stores and changes in management.

She was also moving and unpacking her apartment, which made her replies somewhat inconsistent but we have usually talked/texted for 3-4 hours a day since the first outing.

At one point, she apologized for her sporadic replies and explained that she was still moving things around and trying to get a lot done before work.

I told her I understood and that I had been busy with things throughout the day as well.

I didn't interpret her slower replies as necessarily meaning anything negative because she had a lot going on.

Asking her on a second outing

On October 28, I asked for a second outing. “I’d love to take you out for a proper dinner…”

She responded:

"Lol yea id be down for that"

I then explained that I had meant to ask what kind of food she liked while we were out, but had completely forgotten.

I suggested taking her to a proper dinner and asked what days would work with her schedule.

I also suggested walking at the park beforehand so we could feed the ducks, geese, and other animals.

She said she would need to check her schedule because her days off had changed and her manager was still figuring out scheduling.

She eventually told me that Japanese food was something she was always up for.

I already have a Japanese restaurant picked out.

We settled on a day later this week.

The current plan is:

I'll pick her up around 4.

We'll go to the park first.

Spend roughly an hour walking around and feeding the ducks.

Leave the park shortly after sunset.

Go to the Japanese restaurant for dinner.

Spend approximately 60–90 minutes at the restaurant, depending on how things go.

Where things currently stand

As of yesterday, we have the second outing scheduled for later this week.

Our texting has continued, and we still joke around and discuss various things.

She has shared stories about her family, her interests, and her life outside work.

I enjoy talking to her, and I think we have a good sense of humor together.

I also think she seems comfortable around me.

However, I don't know whether she is romantically interested or simply enjoys spending time with me as a friend.

I haven't explicitly told her that I'm interested in her romantically.

I have invited her to two one-on-one outings, and the second includes dinner, so I assume she may have some idea.

I don't want to put pressure on her, especially because she's been dealing with a lot of work and moving-related stress.

At the same time, I don't want to spend months assuming she knows I'm interested when she might interpret everything as friendship.

What I'm trying to figure out

I'm interested in her romantically and would like to see whether something develops.

I'm not looking to rush into a relationship or make a big confession.

I would like to communicate my interest gradually and see whether she reciprocates.

I'm particularly unsure how to interpret the following:

She used to approach me at work with jokes and non-work questions, sometimes when I was alone.

She enthusiastically accepted the first outing.

She accepted my arm during a haunted house.

We spent time talking together outside the activities.

She picked out a matching shirt for us.

She accepted a second outing involving dinner and a walk.

She continues texting, sharing stories, and joking around with me.

I realize that all of these things could happen in a friendship.

I also realize that accepting two outings doesn't necessarily mean she is attracted to me.

Questions for advice

1. Do you think she is showing signs of romantic interest, or does this mostly look like someone who enjoys spending time with a new friend?

I'm particularly interested in whether the combination of her initiating conversations at work, accepting the outings, and the playful interactions seems meaningful.

2. Do you think she understands that I'm interested in her romantically?

I haven't explicitly called either outing a date or told her I'm attracted to her, but I did try to use language that would make it more obvious. “I’d love to take you out”.

Would you assume she understands, or could she reasonably think I'm just trying to become friends?

3. How would you approach the second outing?

Would you keep things casual and see how the evening develops, or would you make a point of communicating romantic interest?

I was thinking of giving her a genuine compliment when I pick her up and perhaps telling her during dinner that I've really enjoyed getting to know her.

Would that be enough, or would you recommend being more direct?

4. Would you try to initiate physical affection?

She accepted my arm during the haunted house, but I don't want to interpret that as permission for anything beyond what happened.

Would you simply let physical affection develop naturally, or is there a low-pressure way to express interest?

5. Am I overanalyzing the texting?

In the beginning I was the one carrying the conversation but shortly after the first outing it became about  50/50.

She does contribute stories, jokes, and topics, but I don't know whether her texting behavior is particularly indicative of interest.

Would you put more weight on the fact that she accepted two outings than on how frequently she initiates conversations?

6. What would you do next if you were in my position?

Would you simply enjoy the second outing and ask her out again if it goes well?

Would you make your romantic intentions clearer during the second outing?

Or would you wait until another date before saying anything?

I'm interested in honest opinions, including if you think I'm reading too much into things.

Thanks for reading.

 

[Gebidozo]

8 hours ago, Anonymous said:

1. Do you think she is showing signs of romantic interest, or does this mostly look like someone who enjoys spending time with a new friend?

You’ll only know it when you initiate something explicitly romantic and see how she responds to it. You haven’t even kissed her yet, how can one tell?

 

8 hours ago, Anonymous said:

2. Do you think she understands that I'm interested in her romantically?

Judging from your description, possibly not. Obviously people are different, but if I were so hesitant with a woman I was romantically interested in I think she’d just firmly plant me in the friendzone.

 

8 hours ago, Anonymous said:

4. Would you try to initiate physical affection?

Of course. I’d do it on the first date.

You need to show her more clearly that you’re romantically interested. Show, don’t tell. Kissing is the most natural next step. Unless you pass that barrier there is absolutely no way to know whether she is interested or not. She could text you 237823 messages per day and go to 367823 events with you - that’s what women do with their girlfriends and gay friends. It’s all about establishing physical attraction and taking it from there.

 

[ShyViolet]

9 hours ago, Anonymous said:

2. Do you think she understands that I'm interested in her romantically?

I haven't explicitly called either outing a date or told her I'm attracted to her, but I did try to use language that would make it more obvious. “I’d love to take you out”.

Yes, I think your wording made it clear that this upcoming outing is a date.  "I'd love to take you out to a proper dinner", I think that is pretty clear that this is a date.  Friends don't talk like that.  And the fact that she said yes to this, it indicates that she is interested in you as more than a friend.  It sounds like you have both been too shy to make the first move or show your romantic interest, but it is there.

And it also sounds like you are way overthinking this.

[smackie9]

oh MG stop over thinking! Just keep going out spend time together and bond/connect....keep it chill, keep it fun, don't push things. She knows you are interested in her....she's a little hard to read but I'm sure she's thinking of you. Just let things evolve organically. And please don't ask he if you can kiss her, or express your feelings right at her. Just throw in a compliment in once in awhile...the girls do like the light teasing too...just make your time together fun...hold her hand maybe, get a hug in at the end...when it gets too serious too fast it gets icky so relax. 

[flitzanu]

i'd agree with the others.

i think as a softer option if you need one, after this dinner date as long as things go well, you could specifically and literally ask her out again "on a date".  something like "i had a great time, i'd like to take you on another date"

 

[introverted1]

On 11/2/2026 at 11:21 AM, Anonymous said:

On October 28, I asked for a second outing. “I’d love to take you out for a proper dinner…”

She responded:

"Lol yea id be down for that"

I feel as though you signaled that the dinner would be a date in the above exchange.  Friends don't "take" each other out to dinner; they "meet" for dinner.  OTOH, a man who is pursuing a woman romantically, "takes" her to dinner.