Dear Miss A,
A friend who I have had a crush on recently moved to a city 4 hours away from DC, after spending her entire life in Upstate New York. She and I went to college together, but I transferred to another school for my final two years. While we were never really close friends but rather acquaintances, I have always wanted to date her because I always felt like she is a awesome person with shared core values. My question is how do I initiate contact with her and see if she would be receptive to going out on a date with me without scaring her off, or thinking I am so desperate. Aside from an occasional happy birthday wish on Facebook, we haven’t spoken much in the last few years. I know long distance relationships can be hard, but I think she is worth it. Any advice on how to turn this friend into a potential girlfriend?
Dear Wondering in Washington,
It’s not as often that I get questions from men. I really appreciate your writing in. It’s good to for me and my readers (both men and women) to know that men also struggle with love and relationships. It’s also very sweet that you haven’t forgotten about this woman who clearly made an impact on your life, and who you would like to see her again, and develop a relationship with her. I would bet that after spending her entire life in upstate New York and being in a brand new city, she would welcome a visit from an old friend. The prospect of having a woman you really like turn you down is the single most frightening thing for even the toughest, strongest, bravest man.
Since you’ve been admiring her from afar via Facebook, with only the slightest communication, I think that before you ask her out, you should try to engage her a bit more online. Try commenting on her posts, and try to get some back and forth. Then, maybe send her a message on Facebook about a subject she has been posting about. You might include a link to a related article, but make sure to ask a question and engage her. See how she responds. Once you build up some interaction greater than the “Happy Birthday” post, I think you can ask for a date. We’re coming up on the holidays so you will need to do this before mid-November, or else wait until mid-January, as the time of year may make a first date awkward.
In thinking about your first date with her, I don’t think that you should invite her to Washington, because she’d have to drive so far, and would have to get a hotel. You will need an excuse as to why you are going to be in her area. Try searching online for events going on in her city, or a city an hour or so away. Think of hobbies you have (or could pretend to have). Obviously, a gun show wouldn’t be good, but perhaps a boat show, car show, sporting event, conference, expo, or festival. You could also pretend to have won a gift certificate in a charity raffle to a winery, bed & breakfast, resort, or golf course.
The gift certificate idea may be your best bet, as timing won’t be an issue. If you go with an event and then she’s busy that weekend, it would be hard to reschedule. I would simply tell her that you are going to be in the area, and would love to take her to lunch. I think lunch is the way to go since it’s less intimidating. Hopefully, you will like her just as much if not more when you see her again in person.
As a fairly traditional Southern girl, I have no experience in asking people out! I gave it my best though, and hope that this was helpful! Please email me, as I’m very hopeful about your situation and eager to find out how it goes!
– Miss A