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[Standard] Unsure on what to do

#1
Are you male or female:
Male

Is the person your question is about male or female:
Female

What is your age:
23

What are the ages of the other people involved:
23

What is your relationship status:
Single

What is the relationship status of the person you are dating:
Single

How long have the two of you been together:
Known each other - 5 years

Is this an online only relationship:
No

Have you ever had a date in person, face-to-face:
Yes

If this is a long distance relationship, how often do you physically see each other:
Can a few times a month

If you’re engaged, when is the wedding date:
Does not apply

If you’re engaged, but there is no wedding date set — why not:
Does not apply

Are you divorced or just separated:
Does not apply

How long have you been divorced:
Does not apply

How long has the person you are dating been divorced:
Does not apply

How many kids do you each have, and how old are they:
Does not apply

What country do you live in:
United States

Describe any cultural, religious or family influences impacting your relationship:
Families get along, I believe some want to push us together.

This girl and I got to be very close friends in college. We dated some, but it was never serious. We ended up becoming just friends and then spent time a lot together while not necessarily dating. I transferred to another school and we feel out of touch.

Several months ago I moved to start a new job and it's brought me into contact with her family. We've started to talk again and have spent a little time together. Our families get along well together and I know that some of them are hoping for us to be together. I realize that I never got over my crush on her, and seem to like her even more now. We live a little ways apart (2 hrs) but we've talked about getting together for dinner one night.

I'm not sure what to do in this situation. It's very nice to have the friendship back, but I don't want to jeopardize it. I'm not entirely sure she's interested while some of her family has hinted that she seems to be. I think that's more family trying to play match-maker since I'm here with them and she's away. How should I handle this situation?

Re: [Standard] Unsure on what to do

#2
It sounds like you dated, but slid into the friend zone, and now, a few years have gone by, you've graduated from college, and you find yourself only two hours away, wondering what could be. I know you don't want to risk the friendship, but you're at the age where you may lose this opportunity if you don't take it. Imagine if she started dating someone else and it got serious. The friendship you have with her would change. Her focus would be on her boyfriend, and you'd be someone from her past that she sees now and then. I think that it's time to get out of the friend zone and take a risk. You may find out that the two of you really enjoy taking things to a more romantic level at this point in your lives -- and if you don't, then at least you'll have tried. The worst thing you can do is to not give it a shot, and to have regrets. So hedge against that -- and go to dinner with her, and make it romantic. See what's there. You may find your feelings are different, as are hers. As for family match making...
try not to think about your family and her family -- and just focus on what you like about her, and give it a go. You're only two hours away now, and you've both grown, matured, and had some life experience under your belt. Use this potential dinner as opportunity. Meet up, show her a romantic good time, and see if there are any sparks. ;) Seize the day!
April Masini is a relationship and etiquette expert, author of 4 books and the #1 relationship advice forum, blue-chip corporate spokesperson and preferred go-to source for the world’s most prominent media and news outlets.