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Dear Life., Guest Posts, Relationships

Dear Life: Help! Dating Is Hard.

January 20, 2015

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Welcome to Dear Life: An Unconventional Advice Column.*

Your questions get sent to various authors from around the world to answer (and please keep sending because I have like 567 writers that want to answer your burning questions. Click here to submit a letter or email dearlife@jenniferpastiloff.com.) Different writers offer their input when it comes to navigating through life’s messiness. We are “making messy okay.” Today’s letter is answered by A. Wolfe!

Send us your questions because there loads of crazy authors waiting to answer ‘em. Just kidding, they aren’t crazy.

Well okay, maybe a little. Aren’t we all? xo, Jen Pastiloff, Crazy Beauty Hunter. ps, I will see you in London Feb 14th!! Only 5 spots left!

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Dear Life,

I don’t mean to brag, but I’m a pretty cool person. Well, maybe not “cool,” I’ve never been cool (other than for a few inexplicable months in second grade), but I have a lot to offer the world, as a worker, as a thinker, as a friend, as a girlfriend.

The girlfriend part is hypothetical; I’ve never really had a boyfriend. I think I could be a pretty good girlfriend, accounting for a learning curve. And I’ll admit, I don’t come across this brashly in real life, there’s just something about writing that gives me confidence. The point is, I’m a good person, and I think I’d be a good girlfriend. But I’m just terrible at meeting guys! I find myself accidentally leading more and more towards a monastic lifestyle. I work from home, and when I go out for dinner or whatever, I’m usually catching up with a friend and focusing on them, not on trying to flirt with boys. I’ve tried online dating, but I’m not really in an online dating “mood” right now (and I definitely need to be in the right mood for it).

I’m at peace with being single, don’t get me wrong, but I’d like to try having a boyfriend for a bit. In my 23 years on this planet, I’ve occasionally gotten close to a relationship, but never quite reached that point. But please, life, give me the kick in the butt I need to get out there and meet some boys! And some how-to tips would be most appreciated.

K.

Jen Pastiloff is the founder of The Manifest-Station. Join her in Tuscany for her annual Manifestation Retreat. Click the Tuscan hills above. No yoga experience required. Only requirement: Just be a human being.

Jen Pastiloff is the founder of The Manifest-Station. Join her in Tuscany for her annual Manifestation Retreat. Click the Tuscan hills above. No yoga experience required. Only requirement: Just be a human being.

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