June 29, 2015

Should A Woman Ask A Man Out?


Dear Portland,

I like this guy who works for another company in my building.  He actually isn’t that cute but looks have never been high on my list of must have’s but he looks pretty good for a man.  He has a nice personality, a good job and a pretty interesting conversation.  He works two floors down so I usually see him in the work cafeteria, the lobby or walking to and from the train.  He always speaks and walks with me if I see him walking to and from work.  How are you doing? How was your weekend?.. is usually just about the gist of our conversation.

I really think I like him and would really like him to ask me out.  My friends are tired of me talking about him and keep telling me to go ahead and make the first move and ask him out.  They say that this is 2015 and women ask men out all the time.  But I’m afraid and think I should wait for him to make the first move- which might be never.  I’m afraid though.  What should I do?

Should I make the first move?

 Dear Should You Make the First Move,

No.

I know there are those women out there who have thrown caution to the wind and have made that move and have been successful. But I know there are many who have regretted it because as time passed the guy either didn’t treat her the way she expected or if they end up dating seriously- in the back of her mind she will always wonder if he would have asked her out on his own.

Now, about those friends of yours and their advice.  I know they are probably good friends and they mean well but more than likely they are kind of tired of you talking about him and have resorted to giving you bad advice. However, please, please do not allow them to gas you up to do something that is both out of your character and your comfort zone.  Maybe your friends are those girls who ask men out- I’ve got a few of them myself- but I’m just not that girl, and it sounds like you’re not her either.

I’ve heard guys say they think it’s cool for a woman to ask them out and they encourage it… yada, yada.  Those guys are not telling the truth.  Sorry darlin’. Men aren’t telling the truth on purpose, they just think it’s a cool idea and guys usually agree with all -cool ideas- especially if it involves a woman and the potential of a physical connection. I poled two males friends at happy hour and one said he would prefer to ask her out because he would feel more in control of the date; and the other thought it would flattering, to be asked out by a woman but then asked the question… “wait, how she look?”- I cracked up laughing!...but his point was well taken.

Sometimes the ‘universe’ has a way of making us aware and even shielding women from certain men who look good on the outside but may not be good for us. Keep that in mind when you are getting antsy about some guy not making the next move…remember all that glitters may not be gold. Then there are those times when he turns out to be a great guy and you are glad he waited to ask you out because you have those pre-first date memories to laugh about in the future.

My advice to you is to stop worrying and continue being your fabulous self. If you see him in the building or outside- then talk to him like normal. Most of all continue to keep your options open. Then when you least expect it, your interest is redirected to some other man that you meet, at the grocery store or at a festival then this one will either ask you out-not sure why that always seems to happen- be placed in the 'guy you know from work' section of your life or he’ll fade-to-black. Whichever way it works out, I guarantee you will be happy with your decision to NOT make the first move.

 Stay In Your Lane Love,

Portland  

June 24, 2015

My Girlfriend Makes Alot More Money Than Me... Please Help!


Dear Portland,

I've been with my girlfriend for close to a year now, and generally, things are great. I know in my heart that she's the woman I want to spend the rest of my life with. I've even been saving a little while I scope out rings. The only problem is that she makes a lot more money than I do...like A LOT!!! It's not part of our everyday conversation. But the issue does show up from time to time, like when she wants to go out to at a really nice restaurant that I can't afford, leaving her to pick up the check or me offering to split it. The most resent problem came up when she was planning her third vacation with her friends since we've been together. She's paying her way and for her younger sister to go on the trip. Other than weekend getaways to visit my parents or her parents, we've never taken a real vacation together...mostly because I can't afford a trip that would meet her high expectations. She unintentionally made me feel really bad about not having the funds to do bigger things together.
Portland, am I dating out of my league? How will I ever keep up with her if my bank account cannot catch up to hers? Please help...

Five Figure Phil

Dear Five Figure Phil,
 
Yes, you may be out of your league but your girlfriend is most certainly…out of her mind!

Phil, I don’t know any women… in contemporary American society, of any race, on any continent or for that much the universe- including undiscovered and unexplored territories on other planets that would go on 3 vacations, during a calendar year...with a bunch of women- especially if she has a man at home.  REALLY?!

I can't seem to figure out, what women sits on the beach in say Europe, better yet, Barbados (I’m going to assume one of those excursions was to the Caribbean) with that amazing sun, white sand beach, salsa music playing in the distant background, the waiter that you’re boyfriend (you're home, mad-never mind) tipped $15 when you arrived to serve and pay special attention to you both so you don’t have to get up except to get in the crystal clear blue water to cool off. It gets better. Then there’s the lady who gives amazing massages on the beach with cooling aloe vera gel, and I can't forget, the unlimited pina coladas for breakfast (Yaas!), lunch and dinner. All while laying next to your boyfriend, potentially your future fiancĂ©' (oh, right, you’re at home) softly snoring, completely vulnerable, under the umbrella because he’s tired from the countless times in the room…well you get the point. Opps, no you don’t, because you're where? Home!

Who would trade that small slice of heaven to vacay with a bunch of chicks and her little sister?! I’m sorry, were there 3 destination bachelorette parties you forgot to mention? 

Just so we're clear- the occasional girls trip is a must -every few years or so. We ladies need a chance to reconnect and talk about all our girl stuff.  While back at home, our men play airport shuttle; chauffeuring us to the departure gate at BWI and retrieving us from the United baggage claim upon our return.  Yes, we females bond and all that jazz but…it's apples and oranges and definitely should be the second choice compared to a vacation with you.  Being a vacay companion is part of your job description as a boyfriend or girlfriend.  It. just. is.

Is she out of your league?

I really don't know. You said she brought her sister on the trip.  With that statement, I don’t know if you’re implying that you wanted her to pay for you because of your finances (I hope you didn’t mean that) vs. paying for her sister- it’s unclear.  I'd have to know more about you and her to make a better determination. But I can tell you, although money wouldn't be a deciding factor it would play a role. I would base my opinion on your education, background, drive which would all likely provide a good prospectus of your earning potential.

What I do know is- if you really like her- I think you should slow down on the ring hunt and use that money to go on a trip.  If you can’t take a vacay together what makes you think you can spend the rest of your life with her?  Go on at least one trip with her this year- excluding parental visits. No excuses, as there are too many discount internet travel sites and crazy inexpensive cruises available for you to be home while she explores the world.   

Although this relationship seems imbalanced, I really don’t know how long you can both keep ignoring the “elephant in the room” of the significant difference in finances without having a serious talk. Especially since you seem so concerned about it and you’ve been together for less than a year. You don’t say whether you are unemployed or in a low paying job.  If either is your current job status then I’m sure time and diligence will provide you with either a job, or a better one.

But just so you know, there’s always going to be someone in the relationship who earns more money and the man is usually much happier if it’s him. But since it’s currently not you, what’s not cool is you crying broke and she tossing money around like it grows on trees. Saving is important but so isn't spending quality time together and that usually costs money.  So the subject of saving and spending for entertainment etc. should be a part of the "elephant” conversation along with some of your other concerns- and hers too. 

Now, I Need A Vacation Love,

Portland

June 04, 2015

I Miss Being Strong!


Dear Portland,
I miss being strong! When I was younger, I used to have unshakeable faith in myself. No matter how hard things got, or whatever befell me, I always kept trying. I'm still trying, but I lost so much faith my ability to succeed. And I'm worried I'm becoming a jaded cynic. How, besides actually really succeeding at something, can I regain my confidence and faith in myself?

My strong is gone


Dear My Strong Is Gone,
Wow what an honest question!
I applaud you for seeing and admitting that things have changed in your life from positive to somewhat cynical--and you want your old self back. It seems to me that something has shaken your once high self esteem.  You don't mention what that specific thing was or whether it was a series of things in your question but that is what I must assume.  Age, rejection both personal and professional can play a role in moving from a place of yes to uncertainty.  But rest assure you are not the only one.  Many people suffer from this- its called growing up. And yes, sometime it can suck but keeping a positive attitude and not taking life too seriously is something you can consider working on. The fact that you are self-aware puts you heads and tails above the rest. Many people cannot understand their own feelings much less articulate them the way you did. I applaud you for that!
Although you're older now and likely have more responsibilities, try to remember where you were and what you were doing when you had this unshakeable faith in yourself- and try to somewhat mimic that time. For example, in college, maybe you ran track or played on the tennis team and now you've stopped participating in those activities you enjoyed because family and work responsibilities have taken up more of your time?  Or maybe you've abandoned your passion... for singing or dancing? Perhaps take a class at your local community college or volunteer-all communities seem to be in need of people who are willing to donate their time. Choose wisely then start slowly by picking at least one thing that you enjoy and I'm confident that you'll soon be looking at the old new and improved you in no time.

Unshakably Strong Love,
Portland