Ladies, should I ask this person out?

[Wred]

Hi ladies,

I would like your opinions please.

I am really considering asking out the person that cuts my hair. We have really good chemistry and never run out of things to talk about and are always laughing and sometimes having deep conversations as well.

We’ve texted back-and-forth before outside of the salon, sharing playlists and making jokes here and there, not too often but it’s happened a few times.

I guess I’ve known her now for about eight months. She was married and now she is separated, even though mentally, I think she’s been separated for a while and has wanted to get out.

In our state, you have to be separated for a year before you can file for divorce it’s very common for separated people to get out there and date.

I do understand that it’s kind of their job need to be really personable in this profession so you’ll keep coming back, but this does seem like it’s turned a corner.

I’ve also talked to her about a pretty brutal break up that I went through with my fiancé last year where I was cheated on a bunch.

So yesterday, we really got deep and I told her about some of the tragedies that have happened in my life, and she did too.

It was kind of funny because she left me under the heat lamp like three times longer than she should have because she was quite enamored with my story.

What usually takes 30 minutes took like an hour, but we really connected on a deep level and I could tell she was really into it. I know she really likes me a lot just as a friend I guess, or a customer, but I would say we’re friends for sure.

Like most men, I am awful at picking up on hints, or misconstruing normal friendly behavior as possible flirting.

When I was sitting in the chair, she kind of put her hands on my shoulders when she was just telling me “oh I forgot to tell you about something” but she kind of put both hands on my shoulders for a little bit and it had nothing to do with the haircut. I know that much. 

Does that mean anything? I mean I know it would mean that she feels comfortable around me but, who knows if it means more.

I just found out yesterday that she was separated. I have no idea if she’s seeing anybody but I don’t think she is. I’m pretty positive that she isn’t.

But yesterday, we definitely went deeper than we ever had, sharing some pretty intense personal stuff with each other and we were totally dialed in. We also talked about relationships and what we like and don’t like within the context of them.

Our conversations have always flowed like fine wine and our senses of humor certainly match.

One important note: I am 47 years old and she just turned 30. and I have three kids and she has no kids. I have a feeling that wouldn’t bother her though. She already knows.

I’ve been told I look like I’m probably late 30s early 40s, I guess because I don’t drink and act pretty youthful.

However, my late fiancé was the same age as she is. She was also incredibly gorgeous just like this person. so she knows I’ve had a years-long relationship, which was really successful until the end, with somebody her age.

When I shaved my beard a couple months ago she told me it looked really good, enthusiastically, so I guess she thinks I’m attractive? I don’t know. I think she does. I didn’t ask….she was genuinely surprised when I walked in.

So on the way out yesterday, I wanted to kind of move it along just a little bit but without giving away how I was feeling.

Since she was going through a tough time, I said “look, if you ever need to vent, or just wanna talk to somebody, you can reach out to me anytime and I’ll be there to talk to you.”

She said “thanks I really appreciate you and I really enjoy working with you.”

I don’t know, I kept focusing on the “I appreciate YOU” as opposed to “I appreciate IT,” maybe that doesn’t mean anything?

Then today, I had to text her about a future appointment, and she knew it was coming. But I made a couple of jokes and she laughed and I sent her a couple of playlists, which again I’ve done before, and told her that if she’s ever feeling down, or up for that matter, that she can listen to these. It was music that we had talked about and both like.

She gave both of them the love heart reaction, and another “I appreciate you” with exclamation points.

So we like the same music and have talked about concerts a lot. I thought about perhaps asking her to go to a concert with me, there are three around town that we could choose from that I think she would really like.

I don’t really want to present it as like a real date (or should I?), because that comes with expectations, and I certainly don’t wanna sit across from each other at some fancy dinner.

I’m thinking maybe we go and have a great time and then I could follow up and ask her out officially? Or do I let my intentions be known right away, but perhaps not directly to where she feels pressure? I want her to be totally relaxed. 

I thought about doing something with more than just the two of us, like with her friends, but I really wanna avoid the friend zone up front. 

It’s certainly a delicate balancing act.

How do you think I should handle this? Or should I even pursue this at all? 

It does feel different. It feels like, to me anyway, that I could really be something special.

I know confidence is key but I want to be very careful. 

Also, I’ll need to prepare and get advice about what to do if she says no. I think I would kind of act like it was no big deal and be friendly and continue on with the friendship, and maybe it would turn into something later? I’m not sure.

Any opinions would be greatly appreciated!

Thanks

[Alpacalia]

I think she enjoys your interaction but her "thanks I really appreciate you and I really enjoy working with you" in response to your invite seems like a soft no. Now, that can be for a couple reasons. One, that she is not romantically interested or two, that she perceived your question as a non-romantic invite.

She is still technically married, so there's that. 

If you want to consider asking her out again in the future (preferably once her divorce is final), you need to be very clear that if you really want to get things going, you want to take her on an actual date. I'd also caution against placing yourself in a position where you are a sounding board for her romantic woes.

Her marital woes are also not an opportunity or a means for you to become closer to her. 

Edited December 9, 2022 by Alpacalia

[ShyViolet]

Yes, I think it's worth a shot.  You should ask her out.

21 hours ago, Wred said:

Also, I’ll need to prepare and get advice about what to do if she says no. I think I would kind of act like it was no big deal and be friendly and continue on with the friendship, and maybe it would turn into something later? I’m not sure.

If she says no, don't ever flirt or ask her out again.  Don't be that creepy guy who asks a woman out repeatedly trying to "wear her down".  If she says no then you'll have your answer and you'll need to just forget all this.

[Wred]

Oh yeah I definitely wouldn’t. I would do everything I could to get it back to the friendly thing that it is now. The more I think about it I probably will not ask her out.

[glows]

Don’t be stuck in limbo either flirting, spending time texting and sending playlists to someone without biting the bullet and asking them out. 

Understandably you may be hesitant as you’ve just ended an engagement or may be unsure of yourself. Perhaps this is a fun fantasy and her warmth and affection is just initiating you back into the world of dating. 

When you’re ready start dating and asking women out. Don’t stay stuck wasting your time in situations like this when you can be spending quality time dating someone you really like.

[Wred]

Yes you’re right. If I do it will probably be in a couple weeks. There’s just a lot tangled up here right now. I think I have no chance but if it worked out man, it would be so exciting. We will see

[glows]

Why do you think you have no chance?

[Foxhall]

Id ask her to the concert for sure,

time is moving on buddy- these younger women will be out of your reach soon enough- make the most of it while you still can.

all she can say is No

[Wred]

5 hours ago, glows said:

Why do you think you have no chance?

Huge age gap,  she's in the middle of a divorce, I'm a customer, I'm always the one that reaches out first. I don't know. I'll probably just try it and see what happens. Once we're on that first date, I'm pretty confident, it's just getting there

[glows]

You can ask her out as if paying her a compliment. She’ll be flattered regardless, I’m sure. The situation is not ideal so I wouldn’t build up on it like it were to last long or amount to anything. I think you’re taking asking her out too seriously as if it means a relationship has to come out of it. 

Remember you’re just asking someone out to see if there’s mutual interest on the surface, nothing deep.

[introverted1]

On 12/9/2022 at 2:57 PM, Wred said:

She said “thanks I really appreciate you and I really enjoy working with you.”

I think she's setting your expectations with this comment.

[JTSW]

I'd say go for it.

You have a great connection and appear really close.

Just do it. Don't wait.

You got nothing to lose.

Don't be afraid. Bite the bullet.

Age doesn't matter.

[Wiseman2]

On 12/9/2022 at 2:57 PM, Wred said:

She said “thanks I really appreciate you and I really enjoy working with you.”

This comment seems intended to keep you as a good costumer but to underscore that she's not interested in a personal relationship. While "nothing to lose" may on the surface seem ok, it will make things awkward for both of you and put her in an awkward position since she was crystal clear that this is a professional relationship only .