• SumoMe

The Better Half is a no-holds-barred question and answer session with Maria, the resident expert on all things from a woman’s point of view. Maria answers all types of questions related to men’s fashion, grooming, lifestyle, interests, and advice on maintaining the mantra: happy wife, happy life. Maria is a sassy, organized, and accomplished 20-something bibliophile with a Master’s degree who knows a thing or two about improving the lives of men. Maria also writes her own blog, called Forever in Pearls.

If you have a burning question that you want answered, go ahead and ask Maria.

There’s this girl I want to ask out, and we are friends already, but I don’t want her to say no and jeopardize what we have. I think she’s really great, and I’ve heard that once a guy asks a girl out, and she says no, that things get awkward after that. How can I make sure that even if she says no, that we can continue to be friends?
-Ian from Chicago

Unfortunately, there’s no way to guarantee that things won’t get weird after you ask her out. However, you’ll never know what she says unless you take the plunge, so if you have strong feelings for her I definitely encourage you to let her know. You never know, you might end up in the best relationship of your life.

However, if she does say no, then how you act afterwards will make a big difference towards whether you stay friends or not. Story time: I’ve been with my boyfriend for almost 6 years now. Over the course of those 6 years, I’ve been asked out a few times by guy friends who didn’t know I had a boyfriend. After turning them down, I’ve remained friends with some, while others I never talked to again. The ones I’m still friends with all did one thing in common–they didn’t treat me any differently afterwards.

If she turns you down, then don’t shut her out of your life. Things might be a bit awkward for a while, but continue to invite her to hang out with you and your friends just like you used to. Basically, treat her like one of the guys. After a while, you’ll both be able to laugh about “that time you asked her out.”

One of my friends was at a concert recently (outdoor venue, sitting down on blanket) with his family, and sitting next to them was girl and her parents. My friend said the girl was very attractive and seemed to be his type, but he didn’t know how to approach her because her parents were there. His parents and older sister were apparently not helpful. He didn’t have me, or any of our other friends there to help him as a wingman. Is it even possible to approach a girl when she is with her parents? Be it at an outdoor concert, restaurant, sporting event, etc.? If so, how? I’ve asked friends, both male and female, and gotten mixed reviews. I personally think it’s possible, but haven’t thought of anything that would successfully break the ice, for if ever it would happen to him again, me, or any other male. Any thoughts?
-Anonymous from Dallas

My initial reaction is to say that if it’s just the girl and her parents, you’re probably out of luck. If she’s college-aged or older, she most likely doesn’t live with her parents and might not get to see them too often. If that’s the case, the last thing she probably wants is to be approached by a guy when she’s trying to spend some quality time with them. I know a lot of girls would be mortified to be approached by a guy in front of their parents as well.

However, it’s not a complete lost cause, and it is possible to meet a girl with her parents if you’re willing to get creative. If you absolutely must talk to her then there are a few things you could do. The trick is not to approach the girl directly, but approach her family. You said your friend was at a concert at the Arboretum… he could have put on his best, charming, parent-wooing smile, leaned over to her and her family and said “Hi folks, I’m so and so. My family brought wine and hors d’oeuvres but we have too much to finish by ourselves. Would you like to join us? We come to these concerts a lot and it’s always more fun in a big group.” That’s just an example, and it’s kind of cheesy, but the key there is to include her parents as well. These kind of introductions really only work if they’re near you though. It’s kind of weird if you cross the entire lawn just to talk to a family you’ve never met before.

Most likely, they’ll politely decline the offer to join your group. However, the line of conversation has now been opened, and you can make small talk with her and her family about the concert, weather, school, etc. to see if she seems interested in you. If the conversation takes off, then you have a natural segue into exchanging contact info. If not, then you just wish them a good evening and make your way back to your group. If they do join your group, then all your work is pretty much done.

Most likely, they’ll politely decline the offer to join your group. However, the line of conversation has now been opened, and you can make small talk with her and her family about the concert, weather, school, etc. to see if she seems interested in you. If the conversation takes off, then you have a natural segue into exchanging contact info. If not, then you just wish them a good evening and make your way back to your group. If they do join your group, then all your work is pretty much done.

You could also try to find something about them that you could use as a conversation starter. Is her dad wearing an Alabama shirt? Ask them how bad they think A&M will get beat next season. Do they have a dog with them? Tell them that their dog is adorable and ask if you can pet it. Small stuff like that can really help to break the ice.

And if you just want to throw a Hail Mary, you can always walk up to her when you’re about to leave and pull a “Hey I just met you, and this is crazy…” (you know the rest). Her dad will probably give you the stink-eye, but crazier things have been known to work. But in all seriousness, don’t do this unless there are no other options.

XOXO

-Maria