13 posts tagged with dating and shyness.
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The ethics/practicalities of an older woman dating a younger male virgin

[This post contains somewhat graphic descriptions of our intimate experiences and sexual topics generally, so if you are sensitive or perhaps at work it is good to know that.] I am in my early 30s and my new boyfriend is in his mid 20s. I am the first woman he has ever dated, the third he has ever kissed and if we progress in the relationship I will be the first he has ever had sex with. He is a phenomenal human being and I can hardly believe how lucky I am to know him let alone get the chance to have a relationship with him. I am worried about a few things, however and want to weigh them carefully before proceeding any further. [more inside]
posted by telomere on Sep 16, 2013 - 36 answers

Dating advice for shy people?

Dating advice for introverted/shy women (or men!)? [more inside]
posted by anonymous on Oct 28, 2012 - 11 answers

Me : Extrovert. She : Introvert. Can this relationship survive? Should it?

Me : Extrovert. She : Introvert. Can this relationship survive? Should it? [more inside]
posted by Sloop John B on Mar 28, 2012 - 67 answers

How to Get What I Want

How do I, an early-30's woman, get what I want when it comes to dating and sex? [more inside]
posted by anonymous on Feb 21, 2012 - 16 answers

How do a Shy Girl and a Shy Guy Get Together?

How do I approach a shy guy, or how do shy guys like to be approached? [more inside]
posted by oceanview on Dec 30, 2011 - 21 answers

How to ask for phone numbers

How do I ask for a woman's phone number in a non-creepy way? [more inside]
posted by anonymous on Dec 2, 2011 - 43 answers

Overcoming shyness in dating

Can't make a move... should I just talk to her about it? [more inside]
posted by anonymous on May 19, 2010 - 46 answers

How do I at least get a date with a shy guy when I am shy and full of self-doubt?

I like shy boys and grumpy boys. I am shy. How to approach? [more inside]
posted by anonymous on May 2, 2010 - 24 answers

She likes me, but does she *like* me like me?

Late start at dating, and I'm worried that I don't/can't express attraction on dates or around people I like. Halp! [more inside]
posted by anonymous on Nov 18, 2009 - 8 answers

How to Keep Steady?

Please help a fella out with the next stage of his Courtship Reeducation Program: How to stay cool when you can't stay ambivalent? [more inside]
posted by EatTheWeak on May 25, 2009 - 13 answers

ShyGuyFilter: What's my next move with an unassertive guy?

I initiated our hang-out; he enthusiastically responded. The evening started with great conversation and mutual interest-- and then the energy seemed to weirdly wane as the evening went on. To be fair, we had a grueling evening. What now? [more inside]
posted by anonymous on Sep 21, 2008 - 22 answers

How does a decent, caring but impotent and shy guy ever find a girlfriend?

I am a 38-year-old man who has many good qualities (I hope so at least) but two drawbacks which understandably be dealbreakers for most women - I am impotent and I have a small penis (around 4 inches on the rare occasions it is erect), so even if my impotence got treated I am not sure I could satisfy a women. On the other hand, I have heard that it's possible to have satisfactory sex life with a 3 inch penis, but have no idea how that can be. So basically I am what would be a figure of ridicule for many other men, and not exactly a strong candidate to be a boyfriend for most women either. However I know some women while still heterosexual may not want a sexual partner e.g. they may be celibate for whatever reason. And there may even be women who will overlook a sex life without penetrative sex for the right person. I have just come out of a four-year relationship which had lots of affection and companionship but not strong feelings of passion and obviously no sex, but I eventually want another relationship again and believe I have a lot of love to give the right person. How can I find her? [more inside]
posted by anonymous on Mar 23, 2008 - 38 answers

My friend needs a date!

I'd like to help my buddy find a girlfriend. He's 26 and pretty normal, other than the fact that he's never had a girlfriend or even been on a date and he's obviously extremely shy around females. How can I help him? [more inside]
posted by b_thinky on Aug 2, 2006 - 35 answers

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