How to Get Past Shyness and Get a Date

Dear Seduction Insider:

Long Story. NEED HELP. I'm a 28-year-old male, single.

I have a massage therapist that I have known her for 5 or 6 years. When I 1st met her she told me I should come back again next week.

When I did she asked if I had a girlfriend. Would I want a girlfriend? Would I have time for one?

Then I noticed she would sit on the table to give me the massage. Also one time she told me she did not work the coming Monday and I could go over to her place. Apparently I was too shy to take her up on the offer.

Well, life went on and she got hitched. She would still invite me to her parties, and say stuff like, "your legs are cut, we should make a sandwich."

Well, just last March she told me she was getting a divorce. Now leap forward to recent weeks. She told me she was dating again. She also told me she has no problem getting men to notice her.

I also noticed that if I did not answer her emails right a way, she will not answer mine right a way either.

So should I ask her out for a drink or something? If I do when should I do it and how? I know one time she told me I could ask her anything, not just for a date. What do you think? Also I have been single all of my life.

Thank you for all the help.

----


Grant Day Answers:

Time to Get Clear on What you Want to Make Happen

Okay new friend, what we have here is a laundry list of the times, places and ways the girl flirted with you and none of your reactions.

No matter what you've really got going on inside, what comes across is that either you're not that interested and she's sort of stalking you, or you're numb with fear. Hello?

Do you like her? Are you attracted to her? Or do you simply think you should like her because she's made her interest in you so plain and simple? You need to figure this out before you take any action.

Unclear reasons = unclear actions = mixed results.


Why are You Single?

You mention that "you've been single all your life" in a way that makes me wonder if you're more than just single my man. Are you trying to tell me that you've never had a girlfriend, never had a date, and are perhaps a virgin?

I don't bring up these issues to embarrass you, not at all. But it might explain why you're so darn reticent to ask a woman out who is clearly showing that she wants you to.

So maybe it's time to sit down and figure out just why you've always been single. Are you super picky and a girl that passes your muster hasn't passed your doorstep, or are you shy and just haven't gotten yourself out there and given yourself a fair shake?

I'm guessing on the latter (which is what's true for most of us).

Here's the deal, as with every other aspect of life, practice is what makes us good at something. If you've had relatively few dates (or none), and shyness has been keeping you from moving forward with this woman (or any other) it's time you realized that it's very easy to second-guess your life away.

Understand that shyness is the killer, not the possible rejection that could happen. Cause guess what? Rejection happens all the time.

You could call or email this woman and she could finally have gotten fed up waiting for you, or is just in a pissy mood that day, or whatever, and she could say, "no thanks."

Yes, sure rejection stings a bit, but it's not going to kill you. And the more times you screw up the courage to ask a woman out, the easier it's going to get.

Will it ever be super easy if she's super hot? No, but if it was too easy it would mean you were either too jaded or dead.


How to Ask

It sounds like this is a woman who knows what she wants and isn't afraid to go after it, but she's smart to not answer your emails right away if you don't give her the same courtesy.

So don't play games, just go for it, ask her out. If you're too nervous to call just drop her an email with something like "how about a drink next Wednesday?" in the subject line.

Say something like, "I've been wanting to ask you out for some time now, why don't we meet at that cool new place on ____street next Wednesday?"

Ask her for a weeknight, not a Friday or Saturday.

Make the first date very casual but pick some place with great atmosphere so she knows you made an effort, it can even be for coffee instead of a drink, but don't ask last minute because it's very likely she will already have plans.

If she says, "no this week is bad what about next week?" take her up on it, after all she may simply be busy, and she's been trying to catch your attention for some time now.

If she takes her time getting back to you, and you start to get nervous, send her a second email (only one!), or leave another message, and say something like, "Hey, I knows it's taken me years to get it together to ask you out, but I promise we'll have a good time."

Good Luck!

Grant Day