Single Guy in the Philippines? Hire a Wingman!

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Are you a single guy living in the Philippines? I'm specifically addressing the foreigners and expats living in this archipelago of 7,107 islands. Maybe you're doing all right with the ladies, such as my friend Scott B, who recently accompanied us on a recent trip to Guimaras.  But let me tell you about a new expat friend that I've also recently met that needed the help of a wingman. Let's call this new amigo "Jim."

A wingman is a role that a person may take when a friend needs support with approaching the ladies for a date. A guy you bring along that helps you out with the women. He's a man that supports another in approaching a desirable women. 

Now I'm not talking about meeting a "GRO," “Guest Relations Officer," probably found in every province throughout the Philippines. I've never been to the Karaoke bars or other joints these ladies hang out at, but I know they're as plentiful as bribes in a barangay

I received an email from "Jim" the other, bemoaning the fact that he wasn't meeting any nice Ilongga ladies in Iloilo.  I took it upon myself to help the guy. He just wanted to find someone that he could take out to a restaurant occasionally or go to the beach with. 

Jim is 57. Seems to be a nice guy. I was willing to help him out. So while my asawa was bringing my twin nieces, Michelle and April, to apply for a couple of call center jobs in Iloilo City, a plan hatched inside my crazy head. 

I went to a dating website and made a profile for Jim. I simply left messages for several ladies inviting them to meet Jim at the local McDonald's at a certain date and time. What could I lose? I hoped my expat friend wouldn't be pissed, but I wanted to see how my experiment would work out. 

Met Jim at the eatery yesterday. Told him what I had done. Thankfully, he wasn't upset with me. First lady was going to show up at 1 pm. She arrived five minutes early. Had a problem. She didn't look anything like her profile picture. I could tell my friend wasn't very happy.

After a few awkward moments, the Filipina pulls out a brochure for the real estate company she works for. It's a large subdivision in Iloilo City located near our rental home. I took the brochure from her and said I would discuss it with my asawa.

The sales agent then excused herself saying she had to meet a friend that just messaged her. Hmmmm, smart girl. Sounded like the pre-arranged text message to bail a girlfriend out of an uncomfortable situation. This smart Filipina had her own "wingman."

Another pinay, in her early 30's,  was scheduled to meet my single expat friend at two pm. Hopefully the next meeting would work out better. Two o'clock passed. We waited another 15 minutes and decided to visit "The Moon Cafe." I wanted to introduce my friend to the Mexican-inspired food there. My attempt at being a wingman wasn't going very well.

As we walked outside, a cute Filipina accompanied by a younger lady, blurted out "Jim" as we passed by. It was the young woman that was supposed to meet Jim at two. She was running late, or just practicing  "Filipino Time."

I can assure you that my amigo was quite pleased with this pretty pinay. I immediately suggested that the two exchange phone numbers. I asked her if she would like to go to a movie sometime with my American friend. She was agreeable. My wingman status was immediately elevated. She and the young lady with her, a sister, then said their "good-byes" and hopped on a jeepney

I had been at SM Department Store in Iloilo earlier in the day buying a new pair of inside slippers. My asawa and twin nieces were at home assisting our "hot" laundry lady. I passed by the cosmetic counter where a cute Filipina sales girl said to me; "Good morning, sir! How are you today?"

I stopped. "Have I chatted with you, before?" She looked familiar, but in all honesty, I sometimes have difficulty telling the sales associates at SM apart from one another. 

  • "Yes, sir. I was pregnant but I'm back to work."
  • "YOU were pregnant. OK, I remember you. But you are so thin now. Do you have a boyfriend or asawa? " I asked. 
  • "No, sir." (The boyfriend that fathered her child had left.)
  • "Would you like to meet an American friend of mine that lives here?" I inquired. 
  • "Yes, sir, " was her reply.
  • "I'm meeting him later today. We'll stop by and I'll introduce him to you." I advised her.

Next post I'll tell you how the meeting with this single mom went, plus I'll relate our meeting with a Magnolia "chick" working at the SM Supermarket. 

  1. hi dave,having a wingman can really help especially when in a store and you have 12 girls sorrounding you the wingman occupies the 11 others and gathers intelligence and holds off the stampede while the single guys talks to the one he is interested in.Which is hard to pick one because they are all beautiful.

    If you have never been to the phils there are up to 12 sales girls in one department and they are never busy and all want to meet the foriegner and they love to smile and joke with you and the first thing they ask is are you married or have a girlfriend? and when you tell them you are single then the wingman needs to step in and hold them back.

  2. What you say is very true, Scott b, especially in the SM Department Stores. I’ve gone to many a SM Department Store in Iloilo or in the Manila area and have had throngs of cute Filipinas surround me hanging onto my every word, unbelievable. When I tell them I am already married to a beautiful Filipina, I’ve actually heard groans of disappointment (or maybe sighs of relief, I am getting to be an old geezer.) Scott is not exaggerating one bit and neither am I. If you’re a single guy and have never been to the Philippines, what in the world are you waiting for brother? :D Thanks for the input, Scott, appreciate it.

  3. Dave you probably haven’t heard the new Bullseye Bold BBQ Sauce commercials, they are quite funny. Most of them are something like telling your boss what you really feel, etc. But one of them is:
    “Just how bold is the new Bullseye Bold BBQ Sauce? It’s asking your ex-girlfriend to be your wingman Bold.”

  4. That IS pretty bold, Lance the Canadian. :D

  5. Sounds like a fun job…how much does it pay? ;)

  6. I’ve actually had sale ladies flirt with me in front of my wife, which causes a certain amount of discomfort. Of course I get ‘the look’ (all married men know ‘the look’). So much for the demure Pinays…

  7. One day I woke up and I was 43 years old, my marriage of 17 years had ended in divorce (3 years earlier). Sure I tried dating but having a medium income, child support and being on the chubby side, well it was a bad experience, not to mention my wandering circle is small. I decided to wander to the Philippines and it was “shock and awe” the likes of which I may never recover from. I didn’t have a wing man (probably should have) Thanks Dave, great story again.

  8. I helped Jim out for free, Randy. He’s a good guy. I’m working on the follow-up story that will have more details.

  9. I’ve had that problem, too, Mark G., but when the asawa shoots them HER look, they quickly back off. I’ve had instances when we walk past the sales ladies and I hear them say “gwapo,” (handsome) as we pass by, not realizing I understand that word. My asawa doesn’t like that, either. I figure a lot of Filipinas just need eye glasses or new contact lenses. 8O

  10. Any single guy that comes over to the Philippines, Lee, will be in “shock and awe.” The ladies here are amazing, beautiful, kind and don’t mind what a guy looks like. The good ones, like my own asawa, care about your character and not your bank account. The Philippines is a haven for single guy. Glad you liked the story, thanks.

  11. I figured it would cost at least one cold SMB for a good wingman! Your cheap Dave :lol:

  12. Jim did buy me a cold one, Randy. That’s always appreciated. :P

  13. Tom Ramberg says:

    Hi Dave,

    You know Pimp Daddy is a catchier phrase than wingman but just stick with what is comfortable to you. I feel like some of your earlier failures were because you guys violated one of the rules. That rule is that when you hang out with someone while you are cruising for chicks make sure that you are the most attractive and charming. Since I am a pretty politically correct guy I refer to it as the plain chick rule. If you are an ordinary girl then surround yourself with fat ugly wildebeasts so you are the most attractive in the group.
    We all know that Dave is like a Sean Connery/ George Clooney hybrid so this guy didn’t stand a chance unless he had a few tricks up his sleeve. I am sure that Dave was quite helpful as a coach. He probably explained that you carry the roll of quarters in the front pocket not the back. You shift uncomfortably and proclaim that your wallet is too thick. (don’t mention that it is full of coupons) You make sure that you wear your good socks with your sandals.
    I have seen some foriegners that have touted themselves in a wide range of capacities whether they were actually qualified or not. The internet is funny that way! Since Dave is now a seasoned veteren with a proven track record I would like to suggest that he start a service for the terminally shy. Maybe the other readers can offer some suggestions for a name.

  14. Hmmmm, Pimp Daddy, Tom? Probably wouldn’t go well with the asawa, but I admit it is a much catchier phrase. Jim has got his own unique style, and while if I was a modest guy I would disagree with your Sean Connery/George Clooney assessment of me, so I won’t. That said, Jim is doing alright now. He just needed a little coaching and guidance. I like the guy. He’s the “real deal.”

    Yep, if you guys have any suggestions for my wingman biz, feel feel to throw them out. Any wingman stories of your own? Go ahead and share them. And thanks much, Tom. Coming from a guy that gets “wolf whistles” from all the cute Filipinas in GenSan, you’re a guy who speaks with some authority. I bet that Gary Wigle guy might have a tale or two to spin. :P

  15. For those without PI experience yet, what Dave says is in no way an exaggeration. I am fairly old and my gf is young, ridiculously pretty, bright and educated. That in and of itself ought to be more than enough to puff my ego to Trumpian proportions.

    But having my beautiful Pinay warn me before each visit about messing with any other girls falls into the realm of the Twilight Zone. I can hear Rod Serling now. “Consider the case of one Dave W., an ordinary, divorced, balding, middle-aged man, barely making do in the commerce of romantic entanglements. And then one day by happenstance, he takes an unexpected turn, arrives in Cebu, surrounded by beautiful adoring women and finds himself in – The Twilight Zone.”

  16. Thanks for confirming what I wrote about, Dave W. Folks, I’m not exaggerating one iota. Again I ask the question, if you’re a single guy and have never visited the Philippines what in the world are you waiting for? C’mon, get over here! 8O

    Loved your Twilight Zone, Dave. I was a big fan of Rod Serling. Man, that guy was kind of creepy cool.

  17. This post reminds me of a sad story with a happy ending. Years ago in “Po Town” (Olongapo City) there was this single guy who spent his evenings on Magsaysay Blvd, relaxing from the daily stresses imposed upon him at his job. Everyday, after work, he would begin his stroll down this music filled and lady laden avenue looking to satisfy his evening’s needs, wants, and desires. Some days he would accomplish his evening’s ultimate objective in a matter of minutes with little effort on his part (and with only a few peso’s). And one of the most amazing things always happened…he would always return home with leftover pesos in his pocket. After living there for over three years, his wants and needs never changed but he longed for some change. So he worked hard on developing a new strategy and it eventually became his passion…to completely traverse Magsaysay Blvd (all 4 tenths of a mile of it), to experience new music and the different sights of the lady folk at the other end of the Blvd. He heard stories. He even had a friend or two that made it to the ‘end’. Sadly though, he never did make it. To many, it is like ascending Mt. Everest where it takes, strength, persistence and perseverance. It takes extreme willpower and cross training. Some make it, but many don’t. He is said to have found his mate just short of reaching the summit. He never received his “Explorer” badge. But he had reached “his” summit and he was happy. It was said that he just had too much PESOnality to make it to the ‘end’! ;)

  18. I can here the music Dave W! :)

  19. Loved your story, Randy. A single guy has to pace himself in the Philippines. I’m getting reports back from “Jim,” and aside from a scammer or two (one lady on the website was using Angel Locsin’s pic for her profile pic) he’s doing very well as is my other expat friend Scott B, who didn’t need the little coaching and nudge that Jim did. As Gary Wigle would say, “it’s more fun in the Philippines.” :D

  20. I guess as a “Wingman”, the work never lasts long. Once the new arrival cracks and escapes the egg, they absorb things and learn rather quickly. They sometimes even take off running before they even learn to crawl or walk. Then it’s like watching a kid in a candy store! ;)

  21. I need a long distance wingman. Ha!

    I’ve been trying to communicate with some Filipinas online and it just goes nowhere. Most of them don’t seem to say much. Is this normal?

  22. Steve, it’s the ones that say too much early on that you should probably shy away from. Not much “drama” up front could be a good thing or, they may be communicating with several “prospects” at once. Once you get one narrowed down a little, I would think the conversation would pick up. Take your time, ask for photos other than “promo” shots.

  23. i have to comment on the shyness,last night i met a woman from a dating site and she showed up on time even early and we went to eat,she was 31 years old,never married no kids,she has spent her years helping mom raise the kids as the father died years ago.

    This girl is very pretty,her profile pic was honest,anyway we went to eat and she was so shy even at 31 that when i asked her a question she would grab her long hair and cover her face with it and hold it there,she wouldnt even look at me just giggled a bit.

    After a couple hours she took her shield down with the help of 1 beer which was her request and she then wouldnt let go of me,she grabbed my hand and held it,she took my arm and put it around her shoulders and put her head on my shoulder, all night she was constantly carressing my arms and hands and put her cheeks against mine,many of these girls are starved for love and attention and if you treat them as a woman with feelings and dont lie to them and try to use them for all the wrong reasons they will give you their heart.Dont be an a-hole be a gentleman.

  24. I agree that many are starved for affection. It’s something in the West we are not used to – at least not from women. That is men may feel starved for attention, but women generally aren’t. Have fun, take your time and make a good choice. In PI you will have the ability to choose.

  25. One comment Dave, that’s slightly off topic. I am a member of several expat forums. On one popular PI forum if I mention that I am an older guy with a pretty younger Pinay gf, the name calling and moral judgments will fly quickly. On another forum, 5 guys will want me to prove that I really have a young pretty gf (which I won’t do).

    So, I really appreciate your little corner of the expat world where I can be honest and even make a little fun of my situation.

    The truth is Pinays are pretty and many do like “us.” I am glad this is a place I can say that and not hide it.

    Thanks all!

  26. You’re right, Randy. Jim has already stretched his wings and is flying on his own. I’m happy for him. :D

  27. Randy’s right, Steve. I’ve never considered any wingman long distance gig, but in our area, Ilonggas, are known for being shy. As long as no one has hit you up for money, you’re doing OK. You’re not putting Gary Wigle’s pic in your profile photo are you? That might have something to do with your lack of prospects. :D

  28. Dave W., I don’t care if a guy is 60 or 70 years older than his girlfriend or asawa. While on wingman duties for Jim, he had some reservations about the age differences of some of the ladies he was meeting. Frankly, as long as they’re 18 I could care a rat’s behind what other people thought. And yes, you’re right, pinays ARE pretty and we ARE popular here. You’re always welcome here, Dave W. You won’t see me raining on your parade.

  29. Good observation, Randy. I agree with you. The ladies you are communicating with probably do have other prospects they are chatting with. As penpals, my asawa-to-be received mail from guys in prison who would get their letters mailed outside of the joint through the help of some friends. So you see, I didn’t have much competition and with my winning smile :mrgreen: how could I lose?

  30. Scott b, my wife, who you know is also an Ilongga, advises me that the Ilongga women are very shy. I know that when the Tom Cat, my expat friend, met our relative, LenLen, she, too, was extremely shy. Some of the ladies also think their English is not very good and that also may play a part in the equation.

    Happy to hear things went well with you. I think you’re on the right track with your “starved for love and attention” remark. Sounds like you’ve met someone with a lot of character. That’s good. And I’m with you a 100% about treating the ladies like a gentleman. Guys, please listen to Scott b. Don’t be an A-hole. You’re not welcome at this site if you do treat a Filipina like crap. But I know that’s not true of my regular commentators, and I appreciate that. You guys have supported me and helped out our family here when we needed it. You’re the best.

    Good luck, Scott B. Maybe Jim will show up next Thursday at our new hangout, the UR Zone next Thursday, and have a few beers (if he’s not too busy.) You single guys could trade stories.

  31. Well…there is my problem. I *had* been using Gary’s photo. (Just kidding Gary). I’m on a Catholic dating site and they do a good job of keeping scammers off so I haven’t had any problems with them asking for money or pictures that were too good to be true. Although I’m fairly certain I came across a ladyboy the other day. I’m thinking the ladies must be shy and I need to give them more time before giving up.

  32. You’re right, Dave W. Plenty of good ladies here to chat with and go out with. Avoid the ones that ask for money. Treat them right and you’ll have a partner for life. But take your time, like Dave W. advises. You’re on Filipino Time, now, remember?

  33. Whew! You scared me for a minute there, Steve! Gary hasn’t responded so he must be napping or eating lunch at McDonalds. Kudos to you for using a Catholic dating site. Should weed out some of the scammers. Ladyboys? You should go on DateinAsia. I wouldn’t give up. Hang in there. To be honest, I bet you could visit the Philippines on vacation and meet a bunch of nice Filipinas in just a couple of weeks. They’re out there. (Just don’t use Gary’s photo anymore, OK? :D )

  34. Gary may be out shopping for a new profile pic since his has been hijacked! After McD’s though. :lol: :lol: :lol:

  35. Yeah, guess you’re right, Randy. Hope he gets a better mugshot. :D

  36. Dave,
    I’m glad to see you helping out a fellow expat. Hopefully 3 is a charm for me and won’t need your wingman services. I have a good feeling this is the one. Dave Oct is fast approaching and really looking forward meeting you and other expats there. Let me know of anything you, Melinda and nieces/nephews want or need so i can bring it with me. I gave you plenty of time to think of something lol. Take care my friend

  37. Steve,
    Theres some good ladyboys for you on DIA lol. You can hardly tell . Take care

  38. I appreciate the kind offer, PapaDuck. October will be here before you know it. And if you do happen to need any wingman services, let me know. I’m getting daily updates from Jim, and he’s doing great. :D

  39. PapaDuck is right about DIA, Steve. Check out this story I did on them back in February 2011. That said, I have an expat friend that has been meeting some very attractive ladies from DIA, and I’m sure they’re not ladyboys. :D