Have always had online relationships up until now and I may be overthinking it

Hey everyone!

For some background info on me - I'm 29, transman (fully pass as male), and have never had a close distance relationship. I've had 3 quite serious online ones where we have met in person over time, but we were already dating by the time we met. So the whole dating before being a relationship thing is very new to me.

I have had a lot of self esteem issues revolving around my transition, including my weight and general physical appearance, but with hormone therapy the past 5 years I have gotten much more comfortable with myself than ever before.

On to the point of this thread..

I met a girl (26 years old) from instagram which is actually a twin sister of a good friend of mine. I've met her in passing at a few group events, but never got past introductions. In the maybe 2-3 times we've seen each other in the past couple of years, she was married. She also lives in a city about an hour away and we just never bump into each other.

Recently, she's commented on a few things on my Instagram stories and I'd started to do the same. Then it became full conversations and asking a lot about each other. We both joked at how we never really talked before the start of the new year. At this point I wasn't sure if she was still married (her account no longer had pics of them but didn't want to assume) and I was careful to ask about it. She didn't dodge the question at all and was very honest and open about all of it with me. I was relieved mostly because I felt like we were starting to get flirty and only assumed she was now single. I had a post up about getting a +1 for my ex's wedding in Hawaii and she said I definitely have to bring someone really pretty. I said well yeah, that's why you have to come!!

I asked her for her phone number about 2 weeks ago and worked up the courage to ask her to lunch this past Thursday. This girl is extremely busy with grad school, working, church, gym, etc., and I would've been okay with her not being able to make it.

She said yes!

A buddy of mine was excited for me (he knows her and thinks she's great) and wished me luck and to pay attention to her body language. I never even think of this kind of stuff, I've NEVER had a first date with a person I wasn't already in a relationship with!

I'm going to try and put a lot of detail into this if that's okay.

2 days before coming into town she asked if I was still coming to see her, I said yes and she picked a place she tried once and really wanted to take me to. The night before lunch, she texts me wishing for a safe drive as there was a severe storm warning for the following morning. I thought it was very sweet of her to check up on me.

We met for lunch at 11 the next day and I believe it went well. She was very attentive, rarely checked her phone for notifications and ignored some unimportant calls, fixed her hair and clothes often, laughed at some of my lame comments, kept veeeery long eye contact (this one started making me nervous lol) and was smiles all around. She even mentioned skipping her 1 PM class that day! I believe we genuinely had a great time and there wasn't even a moment of awkward silence or a conversation topic that felt like was dragging. We've known ABOUT each other for the past couple of years, but this is our first time spending time alone.

I expected a pretty quick lunch as I know how busy she is, but she suggested coffee afterwards. I drove us both maybe just 3 blocks down and she wanted to hook up her phone to play some music on the ride and complimented on my jacket while touching my sleeve. It was all very cute.

The coffee shop was quiet and much more intimate. We talked about food we love, things to do in the city, love languages, what our goals were for the future, etc. and she also talked more in depth about her divorce the past summer. My heart breaks for her and what she went through.

During this she mentioned how she has very few close girl friends and doesn't spend time with guys. She said that a lot of guys have approached her knowing that she's now single and has avoided them completely. She says she flat out never spends time alone with a man. At this point I felt a little confused and hurt wondering if she saw me as a woman instead of a man as I was sitting right in front of her. She's fully aware I am trans and have called me Sir so I'd like to think she sees me as a man. Anyway I just nodded and said I understood why she'd feel that way.

We spent about 2 and a half hours together before she had to go. I gave her a hug goodbye and she asked me to text her when I make it back home safe. I was really nervous about meeting, but it became relaxing and comfortable quickly.

We still talk now though her schedule is getting even more hectic and I've been trying to keep from distracting her.

She is also moving into her new apartment this coming Saturday and gave me her address. I can't come help her move because of work, but want to send a housewarming gift in the mail so I was thinking of sending a really nice pair of kitchen knives and also a stuffed animal puppy and her favorite chocolates. She said she'd make an excuse to buy some for herself for Valentine's day but I think it'd be a nice and simple gesture to surprise her with some (though I am really skeptical about shipping chocolate).

Do you think I'm reading her body language correctly and that she may be interested? Am I overthinking her comment about spending alone time with men in general? I want to take this slow as she has only gotten her divorce this past summer. I really enjoy her company and want to ask her to dinner. Is that too intimate to ask of her right now? I never mentioned the word 'date' for our lunch, if I ask her for another outing, should I say that it's a date or is that too forward?

Thank you for taking the time to read this!!

Honesty is the best policy in any situation. How well does she know you? The housewarming gift may be better in person. It seem to being going well.

I'm 29, transman We've known ABOUT each other for the past couple of years, but this is our first time spending time alone.

She is also moving into her new apartment this coming Saturday and gave me her address. I can't come help her move because of work, but want to send a housewarming gift in the mail so I was thinking of sending a really nice pair of kitchen knives and also a stuffed animal puppy and her favorite chocolates.

Trying to read tea leaves is a fool's errand. In other words, rather than playing guessing games about where the other person is at and what they are thinking, be straightforward and ask for what YOU want.

If you want a date, then be clear you are asking for a date. That way if they say yes, then you know where you stand. If they say no, then you don't have to whip yourself into all this anxiety wondering, getting excited, investing time in that person, and then getting shot down later on, because that will hurt way worse.

Asking for a date, as in making your intentions clear is what good communication is about and relationships in general are all about good open clear communication.

Honesty is the best policy in any situation. How well does she know you? The housewarming gift may be better in person. It seem to being going well.

Honestly, I'd LOVE to give it to her in person. Maybe I will wait until the next week when I have more time off, though I don't know how to bring up going to her apartment. I'm not sure how well she knows me.. If she asks, I always answer.

Trying to read tea leaves is a fool's errand. In other words, rather than playing guessing games about where the other person is at and what they are thinking, be straightforward and ask for what YOU want.

 

If you want a date, then be clear you are asking for a date. That way if they say yes, then you know where you stand. If they say no, then you don't have to whip yourself into all this anxiety wondering, getting excited, investing time in that person, and then getting shot down later on, because that will hurt way worse.

 

Asking for a date, as in making your intentions clear is what good communication is about and relationships in general are all about good open clear communication.

I appreciate your reply. I understand what you mean about anxiety. It's definitely a nerve-wracking first time experience here. I will be more clear about the next thing being a 'date' to let her know where I am hoping this will go!

Don't ask to go to her apartment. Ask her on a date. A dinner date, maybe a film or if you want to talk, a museum or art gallery followed by dinner or coffee.

And forget all that body language BS. If she wants to spend time with you on dates that's all the "language" you need.

Well clearly she is totally fine with you being trans. Which is a positive! But when you were catching up, were you specific that it was a date? Or do you think maybe she thought you were catching up just as friends? She may have thought it was just friendly because you're also friends with her twin sister? Maybe ask her out again for something more date like? Dinner and a movie? And just see how it goes? How long has she been out of a marriage? If it's not long be careful because she may not be ready to date yet.

Well clearly she is totally fine with you being trans. Which is a positive! But when you were catching up, were you specific that it was a date? Or do you think maybe she thought you were catching up just as friends? She may have thought it was just friendly because you're also friends with her twin sister? Maybe ask her out again for something more date like? Dinner and a movie? And just see how it goes? How long has she been out of a marriage? If it's not long be careful because she may not be ready to date yet.

I'm really glad she is cool with me being trans :) It wasn't clear if it was a date or not so I'd like to ask her to dinner and make sure to specify it as one to see how she feels about it. She's been single since this past summer and I'm definitely okay with taking my time!!