40 year old male virgin wants to date

[Jay2400]

40 old virgin here, never have had sex or been in a relationship or had any friends. A few months ago, I joined a dating website with the primary goal of making friends with women, but also possibly to date. There is a woman,44 who gave me her phone number, we had a conversation over the phone, and we texted every day after that. Then I went out of town, and she texted me have a great time,etc,and sent a picture of a man and a woman holding hands, with a caption that said, “Miss u”. When I came back from out of town, we had a conversation over the phone, and it was then that I told her I was a virgin. Her tone of voice seemed to change. She seemed to be disappointed at that point. She said, “I was so excited, when you left and went to out of town….so excited for you to come back and I could chat with you….. She asked if I thought I would know how to be in a relationship, and how do I see a relationship going if I was in one. She asked if I had ever kissed a woman, and I told her no. At the end of the conversation, she asked me to send her pictures of me and told me she would me pictures of her, which she did as soon as she got off the phone with me. The next day she texted me saying good morning have a great day at work, and that evening she texted,”Hey babe hru this evening,I hope you had a great day. I thought about you a lot today”. This was surprising to me because I thought she was disappointed in me being a virgin and never having had sex before. We talked the next day and I told her I wanted to meet for lunch the following weekend. That next day I texted her asking what she had going on for that day, and she said, “I’m gonna do uber, you didn’t make any plans for me your future wife so I will be working lol.” I said Ha ha, But remember I said we were meeting for lunch next weekend. She said “ Yes, I’m messing with you because it’s sweetest day. That week we didn’t speak over the phone and didn’t text each other much. I texted her on Saturday and said listen I wanted to meet for lunch next weekend but some things happened this week and it doesn’t look like I’m gonna be able to meet you for another couple of weeks. Her response was, “It’s cool I understand. I appreciate the friendship we are building. We still are reading the book together so that’s good”. There is a book that we both are reading and we have committed to reading the first 3 chapters and discussing it together. Also, when I texted her for about the first 10 days of having her number she would often “heart” my texts. For the past two weeks she only “thumbs up” my texts. What do you guys think of all this?

[Gebidozo]

Why have you been delaying the meeting for such a long time?

The very first thing you should do is meet her in person, see how the first date goes, proceed from there.

No positive evaluation can be made based on anything that had happened between two people before they actually met each other.

I find it quite strange, however, that she refers to herself as your future wife. Hopefully, that’s just humor. But if it’s not, please be careful, this is not something a sane person would say seriously at this stage.

[Jay2400]

I delayed it because I'm having some money issues. I was going to buy a new outfit, get a haircut, pay for lunch,etc. and I didn't have the money for everything. Also, I didn't think I was ready to have a date just yet. I'm still in the process of figuring out what is the proper date etiquette, and I wanted more time to think of some topics to discuss during the date and what to say during the date if the conversation gets stale or has too many silences, I'm just being honest. I've never been on a date before, and I wanted to make the best impression possible. And she didn't say future wife in a serious way in my opinion, since she put lol after it.

[mario_C]

There might never be a perfect time to go out on that date, so you might as well do it. I know you want it to be perfect, but the reality is you can only do your best and they need to appreciate that. If they do, you have a match. If not...it was practice for more dates!

You don't have to spend a ton of money on a date. Think of fun affordable things you can do - I had a great date where we hung out in the park, had a picnic, I showed her some guitar chords because she wanted to learn, and we walked around. No second date - whatever charisma is, I have the exact opposite - but we had fun.

Go for that. You'll be the great charmer later. Unless you do nothing.

[ExpatInItaly]

There are plenty of low-cost (or even free) date options. You don't need to splash out to have a nice time. 

Delaying the first meet-up this long will kill momentum, though. Evemtually she will think you are messing her arond or are not interested.  And keep it low-intensity and low-pressure. Be reasonable with your expectations since this is a stranger. You don't know how well you will mesh in person. She seems to be getting a bit ahead of herself already,  so just make sure you keep perspective. 

Enjoy yourrself and don't keep mentioning your lack of experience. Now that it's out there, no need to have another conversation about it at this point. She's keen to meet you so you need to lean into that. 

[smackie9]

Making excuses....you don't have to buy "New" ...thrift shopping is trend right now so go to a consignment store for more current clothing. Go on line and see what's trending....lots of help on tictok, omg there are some great fashionistas on there that can help. I say dress casually but polished. Don't go over board with the venue. A nice cafe near a bookstore or even better a bookstore that has a cafe. You need to get off your butt and get on a date with this lady. She seems receptive, and is being kind to signal you she's comfortable with you so far even tho you have no experience. Get out of your head, and see what's been offered to you. 

[Sanch62]

I agree with the folks above. It makes no sense to scramble around for perfection when there is no such thing. Decide whether you want to get hung up behind a barrier of some fantasy, or whether you want to offer this woman the respect of meeting her with your real self and get to know her, too.

Go grab a coffee together and see what happens.