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Should I ask her out now? Strike while the iron is hot?


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Posted

Only thing stopping me right now is how she recently got out of a relationship. But after tonight, wondering if I should strike while it's hot. Worst that happens is she says no and the friendship is ruined.

 

On the flip side, best that happens is she says yes, we connect well as partners and become BF-GF.

 

I'd say the odds are worth it to try.

 

So, we've been reconnecting lately. I'll call her Lisa.

 

Today I went to a small function and Lisa introduced me to her best friend.

 

L: This is Tek

 

L's friend, E: OHHHHH! THE TEKNOE?!?!

 

Me: .....

 

L: .... *embarrassed and stunned that her best friend would give her away like that*

 

Me: Nice to meet you, E

 

E: Nice to meet you. *looks at her friend* Is this the same Tek you've been telling me about?

 

L: ...

 

E: There is only one Tek right? This the same one?

 

L: Yes...

 

Boy, that was a bit awkward.

 

But is that a clear dead giveaway that Lisa likes me? Or should I not read into it? We have interacted a bit the past week and I could see how Lisa told her best friend about me and the things we did... but her friend's reaction indicated like she wasn't just talking about me, but talking about me as a potential perhaps?

 

I feel like I should do something I've never done before... ask a girl out on a date right away. I might go down in flames, and maybe she's not ready to date... but I truly believe I should give it a shot. What have I got to lose? A good gal friend I enjoy talking with? It's worth the risk.

 

Thinking of calling her up Sunday maybe and asking her out.

Dunno if the timing is proper but what the hell.

 

Another option I have is emailing her best friend and asking her for her opinion. This might make me seem weak, but I would at least get a feel for whether it's worth asking her out or not in the 1st place. I could ask her friend if she thinks Lisa would be receptive to me asking her out.

 

And it would just be a date. Not the end of the world or a wedding set-up...

 

Any feedback here?

 

A). Ask her out directly ASAP

B). Email her friend first and check

C). Do nothing. Let her continue to come to me. Too soon to make a play or move. Go with the flow. Let her have more time to heal up from her last relationship

D). Other (specify)

Posted

You didn't provide a ton of information on the back story, but I think I can give you sound advice regardless. That verbal exchange you spelled out for us doesn't really confirm that she likes you, don't read too much into that. However, I would still strike while the iron is hot as you say.

 

You seem like you're kind of overthinking everything and you would probably be awkward if you asked her out. You need to avoid that at all costs.

 

Definitely don't email the friend. That would be such a lame move, and her friend would absolutely report back to her.

 

What you need to do is ask her to get together. Don't make it seem like a date. Just play it cool, and invite her for coffee or a drink. Don't call it a date and downplay any sort of romantic aspect to it.

 

If you ask her out on a "date" she's likely to throw the "ohhh I just got out of a relationship I'm not ready" line. Don't give her the chance to make her own decision like that.

 

When you do get together, be flirty with her and feel out the situation. Don't be forward about your interest in her but just playfully flirt. And if you're feeling confident, kiss her at the end of it and leave it at that. Don't be awkward about it either by asking her permission or anything. Just lean in and kiss her and smile afterwards.

 

If you have a prayer with this girl, this should work out for you. Capitalize on her emotions. She'll be convincing herself why she should go for you without you even saying a word.

  • Author
Posted (edited)
You didn't provide a ton of information on the back story, but I think I can give you sound advice regardless. That verbal exchange you spelled out for us doesn't really confirm that she likes you, don't read too much into that. However, I would still strike while the iron is hot as you say.

 

You seem like you're kind of overthinking everything and you would probably be awkward if you asked her out. You need to avoid that at all costs.

 

Definitely don't email the friend. That would be such a lame move, and her friend would absolutely report back to her.

 

What you need to do is ask her to get together. Don't make it seem like a date. Just play it cool, and invite her for coffee or a drink. Don't call it a date and downplay any sort of romantic aspect to it.

 

If you ask her out on a "date" she's likely to throw the "ohhh I just got out of a relationship I'm not ready" line. Don't give her the chance to make her own decision like that.

 

When you do get together, be flirty with her and feel out the situation. Don't be forward about your interest in her but just playfully flirt. And if you're feeling confident, kiss her at the end of it and leave it at that. Don't be awkward about it either by asking her permission or anything. Just lean in and kiss her and smile afterwards.

 

If you have a prayer with this girl, this should work out for you. Capitalize on her emotions. She'll be convincing herself why she should go for you without you even saying a word.

 

Thanks man. That's excellent advice and I agree whole heartedly with it.

 

In hindsight, emailing her friend is a definite no-no and strips away my confidence/manhood.

 

Asking her out on a date might be too forward.

 

Going out for a casual 1-on-1 bite though might work, but it's hard to find when. With a date at least you know the purpose. With a casual hang out it's a bit harder to mask it.

 

One thing I noticed is she doesn't talk about her ex around me, which is a good sign. I'm not her gay guy friend, at the very least.

 

Yeah, I need to stay smooth/confident/playful and not overthink things, which has always been my numero uno downfall. Thanks again. I'm sure she and her friend will be talking about the "incident" over the next coming days. Maybe that will help Lisa to continue to see me in that "more than a friend" light. Obviously, she's been reporting good things, and that's always a positive start. I'm excited because if she does like me, or ends up liking me, she'd be the first single attractive girl who I like back that likes me in nearly 10 years. I used to think she was out of my league but actually I think she might be right up my alley. I'd say I'm good enough to win her over, realistically. She did mention a week ago that she wants to stay single for a while to sort her head out. I should respect that, too. I think I'll talk to her enough to keep the connection going, but not overtalk as to become that gay guy friend.

Edited by Teknoe
  • Author
Posted

Major update:

 

I asked her out to coffee Sunday so we can debrief regarding Thursday night. She said yes, and I get the feeling she knows what's up.

 

I am going to break my bad old habit of befriending girls I like hoping to take it slow and eventually they realize I am the one. No more of that crap.

 

Sunday, I am not going to confess my interest in her per se, but I will be real and communicate with her about our boundaries, and whether they are appropriate for where we are at. We've been talking as more than friends lately I feel, so in order to protect her and myself, I want to be honorable and lay it out there on the table. Have an open and honest discussion.

 

Last thing I want is to be close friends with another (single) girl and get into that funky pseudo-relationship pit.

  • Like 1
Posted

It's good news that she agreed to meet you for sure. I have to caution you about the rest of your post though.

 

I know that in your mind, it seems reasonable to "lay it out there on the table". And it will help ease that uncertainty that is gnawing at you.

 

But I would advise against this businesslike approach. It takes the romance, intrigue, and mystery away from her and dulls down the passion. You want her to leave having the same thoughts as you. You want her to be making a post on a forum like this titled "Great date! But where do I go from here?"

 

Essentially, don't force the answers down her throat but make her come to you for those answers.

 

What i would do is treat the coffee date as very casual. Make sure that you flirt with her but don't bring up heavy subjects like "where is this going" and "I want to be more than friends" and that crap. You might feel like a stand up guy for doing it but it's essentially just you grasping for a conclusion.

 

The important thing is to kiss her at the end of the date. You must do this, because it will force her to be unable to friend zone you. It will convery your interest a lot better than "debriefing" will.

 

Good luck, and let us know what happens.

Posted
But is that a clear dead giveaway that Lisa likes me?
No, unless her friend was winking at her...

 

Any feedback here?

 

A). Ask her out directly ASAP

B). Email her friend first and check

C). Do nothing. Let her continue to come to me. Too soon to make a play or move. Go with the flow. Let her have more time to heal up from her last relationship

D). Other (specify)

D.) You should have drawn her friend aside and tell her "I'm dying with curiosity now... what did she tell you about me?" Anyway, you missed the chance and are past that.

 

I asked her out to coffee Sunday so we can debrief regarding Thursday night.
Debrief? Really? Don't even mention that or hint at that in any way during the date, which by the way didn't sound like a date, right? You didn't make it obvious it was going to be a date... Fine. You didn't want to go that far yet.

 

She said yes, and I get the feeling she knows what's up.
Maybe.

 

I will be real and communicate with her about our boundaries, and whether they are appropriate for where we are at.
That is to say?? What boundaries do you want to talk about? And are you seeking for her approval? I'd say that's not a good idea.

 

We've been talking as more than friends lately
Can you expand the concept? How did you talk as more than friends?

 

I would advise against this businesslike approach.
I AGREE. It's not business.

 

What you arranged is not a real date... so your next goal should be arranging a real date at night. But pay attention to her clues, to know if she's interested in you that way.

  • Author
Posted

quick update:

 

Met her for coffee sunday to talk about our relationship, seeking clarity. She said right away "Can we just stay friends?"

 

That was quick, easy and over with. Good, too. Now I know. I'm glad I didn't wait around and get my feelings all wrapped up. It's a step in the right direction for me.

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