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Older Filipina Woman

ChickenWing

Space Monkey
space monkey
Joined
Nov 15, 2019
Messages
11
Hi,

I want to hook up with a 60 something year old Filipina milf that works a few offices down from me. We've been acquaintances for about 6 years now. She's closing her business in less than a year and I want hook up with her before she's gone.

I can't figure out what are some ways to escalate and move towards what I want with this woman.

If anyone has been in this situation or would like to offer advice I'd appreciate your wisdom.
 

Chase

Chieftan
Staff member
tribal-elder
Joined
Oct 9, 2012
Messages
6,352
@ChickenWing,

How old are you? That context might help a bit.

She's a bit less than 2x my oldest but if you're close to her in age I would expect just a normal approach ought to do the trick. If much younger... you would need to talk to some of the guys on here experienced with going for older women about how you get around whatever reservations they may have (I assume a gal who's not a straight-up cougar would have some... but maybe they won't?). Colt's articles on this might help:




If you're close in age, I can tell you the path of least resistance is just to wait until her business is almost closed, then make a move then. It's common / easy to sleep with coworkers, etc., when one of you is on the way out... many of the objections to it disappear in that case.

If you don't want to wait that long... then invite her to happy hour with you and get some conversation and flirtation going on, then tell her this is fun, we should hang out outside work more often, when she agrees, tell her maybe something soon, when she agrees to that, take her contact, and tell her you'll text her. Then text and set up the date.

If she won't do happy hour / the hours don't line up right, inviting her to lunch is another perfectly workable option.

Just look out for the "girl you invite to lunch who then invites other colleagues along too" hiccup... that one got me a couple of times in the working world. Always a let down!

Chase
 
a good date brings a smile to your lips... and hers
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