Gents,

So I'm about a month out of a year long relationship that I ended after I realized we both were more interested in other people instead of each other. So I'm single now and there is a lovely lady that I have always had been interested in and it's just so that as far as I know, is single.

I always have a problem asking women out. I will ask her out tomorrow night, after we're done instructing new volunteers.

I just need manly encouragement to make sure I go through with it. I need to do it and get it over with and find out if she's interested or not so I can stop being all antsy and anxious.

Please!

- Dan

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Go for it! I'm sure she'll say yes, just be your gentlemanly-self. Ladies always love a gentleman.

Do you already have a plan for what you'd like to do?  If so, tell her what your plans are.  Then tell her you'd like her to join you.  It will alleviate a lot of the stress.

Well, the plan was ask her out to the range and then to dinner (she's a gun nut like me). I could couch it that way.

Perfect. "I was planning on heading out the range on Saturday for some target practice, then maybe get some italian food at this place I really like - I would love it if you would join me."

Excellent.

Thanks fellas.

+1

Great suggestion. 

Look at you, you sexy bastard! Her answer will be "HELL YES!"

+1

Dan, your value as a man is not dependent on her response to you. If she says "no", your value is the same as it was before she opened her mouth. You're a worthwile person regardless of whether she accepts your invitation or not.

When you know that and you FEEL that, you can talk to her with confidence.

By the way, you don't necessarily need to face a blunt rejection. You can let her indicate interest, or not, and still save face. It also sounds like you're not 100% sure she's unattached. You can find out without asking.

"I'd like to pursue an active social life again. I'd like to ask someone out now and then, but whenever I meet a lovely lady--someone like you--I always think she must already be taken."

Pay attention to her response. S

Oh, my value as a man is certainly independent of that. My value is based on many things, but whether this woman finds me interesting has nothing to do with that. My value rises daily in fact, it feels like these days I'm walking taller, running farther, and generally happier. 

I am back at up-front conversations like this. I hate calling people on the phone for the first time. I hate walking up to strangers. I hate asking women out. It's just a mild social phobia (which I wager is fairly common) that I have to push myself through. 

I'm 99% positive she is single. We've been acquaintences for about 2.5 years, and a year and a half ago I expressed interest while she was breaking up with her boyfriend. I did some dumb shit and ended up with someone else. 

In the intervening year, I've changed and my co-volunteers have also noticed that there is a good possibility that she is interested in me. For example she's been volunteering to help me with nearly everything that I run, wanting to go on visits and even offering for me to keep my bicycle at her place instead of at my ex's where it still lives.

I figure, I ask her out to go do something fun outside of the organization instead of always hanging out while we're volunteering is the right way to go.

The rejection itself doesn't bother me. It's actually preferable to the anxiety that proceeds the question. 

Dan, your value as a man does not depend on her response. Know that, and FEEL that.

You can gauge her interest, and find out for sure whether she is available, while saving face if she's not. It might strike her as a tad coy, but hey, a gentleman has his pride too (wink).

"I'd really like to start an active social life again. I'd like to spend more time with friends, and go out on some dates on a regular basis. I've met some fascinating people I'd like to spend more time with, but every time I talk to a lovely lady I keep thinking something like (dramatic pause) 'What's the one thing you would want to know about me, to want to go out with me for dinner and a show?'"

Just look at her intensely. She will probably give away some reaction. Don't feel the need to say anything for a long time. She might speak to try to break the tension. She might even ask you out!

Allow the conversation to flow in whichever direction it goes. If it goes positively, pursue. If negatively, casually move on to something else, as if nothing had happened.

DO NOT SEEK REASSURANCE FROM HER. Do not seek approval. Don't talk too much! Whoever is more desperate for approval does more of the talking to seek approval. Ask slighty leading questions, let her do most of the talking (80%!!), and pay CAREFUL attention to her emotional "hot spots". Pursue those.

Go get 'em, champ! (wink)
Double post due to strange interaction between my keyboard and the forum software, sorry!

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