A
male
age
41-50,
*hoenix444
writes:OK, I have 2 really big crushes. Lets call them Rachel and Sarah. I’m back in college after over 10 years and find myself fallen for 2 of my classmates both in separate classes. Today as I’m in the cafeteria I find them both sitting together and they’re great friends. I see notice Sarah first and ask if I can sit only to notice Rachel sitting by her side. Sarah knows I’m older (33) and Rachael doesn’t. My query is I know Sarah is single but may be interested in someone else and my nearly stops when I see Rachel. I have class with Sarah tomorrow and since I like both of them I’m not sure what to do. Do I find out if Rachel is single by asking Sarah or ask Sarah out. I’m perplexed and unsure what to do. At 33 I don’t know if I’m too old to ask either of them out but I know I probably will. Anyone want to give some good advice?
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male
reader, Fatherly Advice + ♥, writes (3 October 2013):
 Phoenix,
At 33 you are too old to be asking this question. So I've got to assume you lack experience. I on the other hand am so old that I am out of touch with current trends. So take my advice carefully.
Here is how I see it in order of highest probability of success. But first my assumptions. Sarah and Rachel are both upperclassmen (not freshmen) Sarah is dating the some one that you say she "may be interested in". Sarah and Rachel are close friends.
1) Snoop around some more and figure out what Rachel's status is. Then ask Rachel out if appropriate. This assumes Sarah is unavailable now and allows you to be interested in her friend. A slightly lower probability of success if you ask Sarah what Rachel's status is.
2) Hang out with both of them as frequently as possible. Don't express preference to one or the other. When you have determined which one is most available you can make your decision. This option in the past would get you into trouble with both, but I think it is acceptable now.
3) Follow your heart and ask Rachel out without knowing if she is available.
While I want to agree with Tisha, because she is right it's just a date not a commitment, I can't in good faith recommend that you date two girls who are close friends. You will end up with both of them hating you. Sarah in fact may already have "claim" on you by virtue of having had prior conversations with you. The whole situation is a minefield. A sensible man would stay as far away as possible. Unfortunately your heart is already smitten and something is going to happen. Your best hope for success with R is to wait until S is committed to someone else. Your best hope for success with S is to avoid R altogether.
FA
A
female
reader, Tisha-1 +, writes (3 October 2013):
 Ask Rachel out and ask Sarah out. Going on a date doesn't mean you are getting married or have committed yourself to someone to the exclusion of all others. It just means you are going on a date.
Are Rachel or Sarah very young?
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A
female
reader, like I see it +, writes (2 October 2013):
 You're not too old to ask.
You are however old enough that whichever girl you ask may be wary of the age gap (assuming they're both early 20's college students). As young adults they are just starting to get a sense of who they are and what they want in life. At 33 you are more experienced, farther along in your life achievements, and most likely more set in your identity. They may assume you will be in more of a hurry to settle down and build a life with someone than they are currently - it's not an unusual disparity in age gap relationships.
What you need to do, though, is decide on one or the other. Assuming both are single, which one do you prefer? Ask that one, because the other one doesn't want or need to be settled for.
And whatever you do, don't turn around and ask out your second choice if the first girl turns you down... because guaranteed whichever one you ask will mention it to her friend, whether she takes you up on it or not. Asking both will just look creepy, like you want a younger woman and don't really care which one, and it's likely that both will feel awkward trying to remain friends with you after that.
Good luck with whichever girl you go for :)
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